synergistic lewis base and anion-binding catalysis for the ... · 173.288 154.657 141.310 132.778...
TRANSCRIPT
Synergistic Lewis base and anion-binding catalysis for the enantioselective vinylogous addition of deconjugated butenolides to
allenoates
Vikas Kumar and Santanu Mukherjee*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, INDIA
SUPPORTING INFORMATION: PART B
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-2
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
031.
030
1.04
81.
066
1.11
31.
254
1.28
21.
292
1.31
01.
328
2.89
42.
912
2.92
92.
946
2.96
32.
981
3.31
13.
329
3.34
73.
365
3.66
53.
682
3.70
03.
716
3.73
43.
792
3.80
93.
827
3.84
53.
864
5.75
85.
781
7.26
17.
617
7.80
67.
829
7.96
7
9.44
7
3.09
19.
033
3.15
8
1.04
7
1.03
21.
085
1.07
7
1.00
4
1.00
01.
074
2.03
8
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
12.6
9114
.476
27.3
10
36.7
5740
.286
43.5
23
60.2
75
76.8
4477
.162
77.4
79
118.
533
118.
568
118.
605
119.
158
121.
869
124.
442
124.
474
124.
581
127.
292
131.
454
131.
787
132.
121
132.
454
140.
432
171.
569
181.
768
NH
NH
SN
O
Et
Et
CF3
CF3
NH
NH
SN
O
Et
Et
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-3
-3-2-110 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
040.
720
0.73
60.
797
0.81
30.
904
0.92
10.
945
0.96
11.
109
1.84
71.
864
1.88
11.
898
1.91
51.
931
1.94
92.
053
2.06
82.
085
2.10
22.
120
2.13
72.
505
2.52
32.
538
2.55
73.
032
3.04
93.
068
3.08
53.
536
3.55
73.
572
3.59
33.
634
3.65
23.
667
3.68
55.
787
5.81
17.
260
7.64
67.
805
7.82
77.
973
9.42
4
3.14
23.
195
6.43
59.
370
1.03
01.
024
1.00
8
1.00
7
2.03
8
1.00
5
1.01
11.
003
2.04
9
1.00
0
220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
19.7
420
.41
20.5
120
.66
26.6
327
.38
28.0
937
.81
53.8
156
.74
60.4
4
76.8
477
.16
77.4
8
118.
8311
9.11
121.
8112
4.52
127.
2413
1.81
132.
1313
2.47
132.
8214
0.21
172.
48
181.
09
NH
NH
SN
O
i-Bu
i-Bu
CF3
CF3
NH
NH
SN
O
i-Bu
i-Bu
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-4
-19 8 7 6 5 4 3 2 1 0 ppm
-0.0
020.
777
0.79
30.
869
0.88
50.
903
0.93
80.
954
1.09
31.
875
1.95
51.
972
1.99
02.
005
2.03
22.
180
2.35
42.
636
2.65
52.
669
2.68
83.
063
3.07
93.
100
3.11
53.
511
3.53
43.
547
3.56
93.
693
3.71
03.
726
3.74
34.
945
4.96
86.
622
6.64
57.
264
7.44
07.
826
8.45
8
3.07
56.
475
3.15
79.
000
2.06
9
0.99
8
0.99
3
1.00
01.
005
1.00
6
1.00
0
0.99
4
2.00
9
0.98
2
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
19.3
5020
.294
20.4
6020
.645
26.9
4127
.065
27.7
8836
.776
54.0
6155
.978
56.9
75
76.8
3977
.157
77.4
74
115.
543
118.
841
119.
323
122.
037
124.
745
127.
482
131.
767
132.
100
132.
431
132.
778
141.
310
154.
657
173.
288
NH
NH
ON
O
i-Bu
i-Bu
CF3
CF3
NH
NH
ON
O
i-Bu
i-Bu
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-5
10 9 8 7 6 5 4 3 2 1 ppm
0.00
1
1.12
2
4.23
54.
248
4.27
24.
284
4.44
24.
457
4.47
84.
494
5.05
55.
077
6.51
07.
166
7.18
37.
206
7.21
77.
226
7.24
47.
260
7.56
87.
887
7.92
67.
947
9.10
5
9.02
8
1.02
01.
118
1.00
0
0.96
9
2.17
53.
026
0.99
82.
070
0.93
2
0.99
2
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
27.3
31
35.3
46
44.2
38
66.4
32
76.8
4177
.158
77.4
76
118.
650
119.
059
121.
770
124.
414
124.
481
127.
197
127.
469
127.
586
127.
783
128.
008
128.
699
128.
802
128.
934
131.
312
131.
646
131.
980
132.
314
136.
475
140.
141
172.
168
182.
076
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-6
-3-2-19 8 7 6 5 4 3 2 1 0 ppm
-0.0
071.
035
1.11
01.
128
1.14
61.
169
1.19
01.
198
1.29
51.
313
1.33
11.
357
1.36
51.
594
1.61
61.
627
1.66
41.
705
1.72
91.
738
1.99
42.
019
2.96
22.
980
2.99
83.
014
3.03
13.
049
3.29
63.
314
3.33
23.
350
3.36
83.
386
3.67
03.
718
3.73
63.
754
3.77
33.
790
3.80
73.
825
5.59
85.
622
6.10
16.
119
6.55
17.
260
9.11
03.
340
2.28
25.
112
4.29
22.
074
1.00
01.
049
2.96
6
0.96
8
0.98
9
1.03
7
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
12.9
3114
.687
24.8
7924
.935
25.6
0327
.072
32.8
6732
.966
36.5
1440
.020
43.0
1752
.681
59.8
70
76.8
4477
.162
77.4
80
171.
431
181.
062
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-7
10 9 8 7 6 5 4 3 2 1 ppm
-0.0
04
1.11
51.
587
1.61
81.
643
1.67
31.
985
2.01
92.
046
4.88
54.
908
5.63
2
7.25
87.
545
7.91
28.
098
8.11
7
8.73
8
9.07
6
6.54
0
9.23
1
1.00
0
0.99
2
1.08
5
2.08
50.
991
0.97
2
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm
27.6
2129
.378
34.9
9136
.203
41.8
15
53.5
68
67.0
87
76.8
3877
.155
77.4
73
118.
437
118.
473
119.
124
121.
836
124.
216
124.
231
124.
549
127.
261
131.
163
131.
497
131.
831
132.
166
140.
027
171.
553
181.
801
NH
NH
S
O
NH
CF3
CF3
NH
NH
S
O
NH
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-8
11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.98
61.
039
1.05
61.
074
1.08
11.
099
1.11
73.
000
3.01
83.
035
3.05
13.
069
3.08
73.
214
3.23
13.
249
3.26
83.
286
3.30
33.
565
3.58
23.
600
3.61
23.
619
3.62
93.
637
3.64
53.
663
3.68
05.
040
5.06
5
7.65
78.
068
8.32
98.
354
10.4
79
9.93
53.
039
3.12
6
1.09
41.
207
2.06
1
1.00
9
1.01
7
2.04
21.
005
1.00
0
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.1
7714
.920
26.2
0336
.467
39.2
8139
.489
39.6
9839
.907
40.1
1540
.239
40.3
2440
.533
42.7
3459
.058
115.
100
118.
431
119.
473
122.
182
124.
892
127.
604
131.
300
131.
627
131.
954
132.
281
141.
516
162.
968
168.
866
169.
129
180.
718
184.
632
OO
NH
NH
N
O
Et
Et
CF3
CF3
OO
NH
NH
N
O
Et
Et
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-9
-110 9 8 7 6 5 4 3 2 1 0 ppm
0.93
50.
990
0.99
71.
008
1.02
61.
043
1.05
51.
073
1.09
02.
963
2.98
02.
997
3.01
33.
031
3.04
83.
196
3.21
43.
232
3.25
13.
269
3.28
73.
438
3.49
63.
522
3.53
93.
556
3.57
33.
591
3.60
63.
624
3.64
14.
863
4.87
84.
901
4.91
74.
922
4.93
94.
961
4.97
75.
007
5.03
27.
946
7.97
18.
052
8.07
0
9.06
13.
108
3.09
5
1.06
31.
062
2.09
3
3.08
6
0.98
34.
000
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
0314
.935
26.2
6527
.566
36.3
4239
.295
39.5
0339
.712
39.9
2140
.129
40.3
3840
.546
42.6
3346
.219
58.3
92
119.
647
121.
676
121.
713
122.
336
125.
049
127.
787
128.
952
128.
983
130.
465
130.
791
131.
117
131.
441
142.
816
167.
500
167.
745
169.
238
182.
884
182.
942
OO
NH
NH
N
O
Et
EtCF3
CF3
OO
NH
NH
N
O
Et
EtCF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-10
11 10 9 8 7 6 5 4 3 2 1 ppm
0.97
91.
031
1.04
61.
065
1.09
0
3.00
63.
022
3.03
83.
054
3.22
33.
241
3.25
93.
276
3.58
93.
605
3.62
0
5.05
95.
083
7.61
87.
637
7.67
47.
693
8.32
18.
344
10.2
41
9.09
76.
009
1.04
61.
075
1.92
2
1.01
8
4.07
5
1.00
2
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
0114
.952
26.2
5636
.453
39.2
7439
.483
39.6
9239
.900
40.1
0940
.209
40.3
1840
.526
42.7
1658
.966
118.
425
120.
826
122.
422
122.
741
123.
061
123.
382
123.
521
126.
217
127.
041
127.
077
128.
911
142.
999
163.
415
168.
927
169.
045
180.
472
184.
616
OO
NH
NH
N
O
Et
Et
CF3
OO
NH
NH
N
O
Et
Et
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-11
11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.97
01.
022
1.03
91.
057
1.06
81.
086
1.10
32.
492
2.97
92.
995
3.01
33.
029
3.04
63.
063
3.20
03.
217
3.23
53.
254
3.27
23.
289
3.34
33.
541
3.55
83.
575
3.59
33.
610
3.62
53.
642
3.65
93.
716
5.06
45.
089
6.90
16.
923
7.36
17.
383
8.13
08.
153
9.85
7
9.20
96.
190
1.04
21.
087
2.07
53.
033
1.00
1
2.03
9
2.02
7
0.98
8
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
13.2
5115
.000
26.3
0536
.415
39.2
9039
.499
39.7
0839
.916
40.1
2540
.334
40.5
4242
.702
55.6
7558
.761
114.
969
119.
960
132.
650
155.
673
163.
895
168.
267
169.
144
180.
729
183.
259
OO
NH
NH
N
O
Et
Et
OMe
OO
NH
NH
N
O
Et
Et
OMe
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-12
-2-110 9 8 7 6 5 4 3 2 1 0 ppm
0.92
91.
007
1.02
41.
042
1.06
61.
083
1.23
81.
265
1.28
31.
302
1.31
31.
341
1.65
11.
864
1.89
02.
950
2.96
72.
984
3.00
13.
018
3.03
53.
188
3.20
53.
223
3.24
13.
260
3.27
73.
315
3.50
83.
525
3.54
33.
561
3.57
73.
594
3.61
03.
627
3.64
43.
758
3.76
44.
993
5.01
87.
710
7.72
97.
791
7.81
6
9.45
86.
533
6.06
12.
005
2.19
9
1.12
81.
235
2.18
71.
165
1.00
0
1.02
20.
994
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
2414
.952
24.1
6425
.200
26.2
9233
.862
34.0
1736
.249
39.2
8139
.489
39.6
9839
.907
40.1
1540
.324
40.5
3242
.592
52.1
8458
.286
167.
128
167.
244
169.
387
182.
167
182.
527
OO
NH
NH
N
O
Et
Et
OO
NH
NH
N
O
Et
Et
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-13
-2-111 10 9 8 7 6 5 4 3 2 1 0 ppm
0.71
30.
730
0.81
70.
833
0.86
50.
878
0.89
30.
974
1.81
31.
830
1.84
71.
864
1.88
21.
891
1.90
01.
918
1.93
51.
952
1.96
81.
986
2.57
62.
595
2.60
92.
628
3.03
03.
046
3.06
73.
082
3.34
03.
363
3.37
73.
399
3.68
03.
697
3.71
33.
730
5.12
85.
152
7.61
47.
635
7.66
57.
687
8.34
28.
366
10.2
67
3.17
83.
544
6.23
29.
050
2.21
3
1.00
61.
052
1.05
81.
047
1.07
0
4.07
7
1.01
7
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
19.1
6220
.244
20.6
8620
.765
26.3
3226
.659
27.7
5036
.920
39.3
2739
.535
39.7
4439
.953
40.1
6140
.370
40.5
7953
.227
56.0
1259
.228
118.
444
120.
831
122.
443
122.
763
123.
081
123.
400
123.
525
126.
220
127.
039
127.
074
128.
916
142.
997
163.
362
169.
146
170.
165
180.
504
184.
586
OO
NH
NH
N
O
i-Bu
i-Bu
CF3
OO
NH
NH
N
O
i-Bu
i-Bu
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-14
10 9 8 7 6 5 4 3 2 1 0 ppm
0.94
91.
001
1.02
51.
042
1.06
11.
080
1.09
82.
502
2.50
62.
919
2.93
42.
952
2.96
82.
985
3.00
23.
197
3.21
43.
232
3.25
13.
269
3.28
83.
330
3.53
43.
551
3.56
93.
588
3.60
63.
622
3.64
63.
663
3.68
03.
696
3.71
43.
730
5.04
15.
066
8.19
18.
216
18.0
0012
.226
2.11
02.
097
2.04
01.
960
1.96
8
1.94
7
200 180 160 140 120 100 80 60 40 20 ppm
12.8
1414
.572
25.9
1236
.055
38.8
9339
.102
39.3
1039
.519
39.7
2739
.936
40.1
4542
.151
57.8
56
166.
623
168.
773
182.
151
OO
NH
NH
N
O
Et
EtN
O
Et
Et
OO
NH
NH
N
O
Et
EtN
O
Et
Et
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-15
11 10 9 8 7 6 5 4 3 2 1 ppm
0.97
6
2.90
03.
097
5.15
55.
180
7.65
78.
072
8.28
48.
309
10.4
68
9.09
2
3.05
03.
032
1.03
0
1.00
8
2.00
00.
997
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
26.1
5435
.447
36.4
3038
.209
39.2
9939
.508
39.7
1639
.925
40.1
3340
.342
40.5
5158
.910
115.
210
118.
434
119.
501
122.
216
124.
929
127.
642
131.
292
131.
620
131.
949
132.
276
141.
528
162.
913
169.
240
169.
778
180.
704
184.
838
OO
NH
NH
N
O
Me
Me
CF3
CF3
OO
NH
NH
N
O
Me
Me
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-16
11 10 9 8 7 6 5 4 3 2 1 ppm
0.97
81.
774
1.79
01.
805
1.84
01.
859
1.87
51.
890
3.31
13.
343
3.47
63.
497
3.58
6
4.87
84.
903
7.64
08.
054
8.27
88.
303
10.4
26
9.48
4
4.39
0
2.63
52.
082
1.03
3
1.00
1
2.04
81.
002
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
24.1
7025
.973
26.1
2336
.176
39.3
1039
.518
39.7
2639
.935
40.1
4440
.352
40.5
6145
.934
47.4
1961
.610
115.
143
118.
387
118.
415
119.
474
122.
186
124.
899
127.
611
131.
280
131.
607
131.
934
132.
260
141.
525
162.
877
168.
053
169.
323
180.
741
184.
776
OO
NH
NH
N
O
CF3
CF3
OO
NH
NH
N
O
CF3
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-17
10 9 8 7 6 5 4 3 2 1 0 ppm
0.98
71.
384
1.41
01.
432
1.45
81.
748
1.76
51.
773
1.79
21.
960
1.98
62.
019
2.02
82.
039
2.49
72.
500
3.33
43.
521
3.54
03.
565
3.58
54.
456
4.47
34.
774
4.80
04.
965
4.98
24.
999
6.94
56.
962
6.97
97.
111
7.13
17.
149
7.15
97.
183
7.19
77.
700
7.72
27.
743
7.76
58.
013
8.03
8
10.2
11
9.01
0
1.10
12.
099
2.18
3
0.92
2
0.98
71.
018
1.03
3
1.07
39.
167
4.07
41.
007
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
0114
.952
26.2
5636
.453
39.2
7439
.483
39.6
9239
.900
40.1
0940
.209
40.3
1840
.526
42.7
1658
.966
118.
425
120.
826
122.
422
122.
741
123.
061
123.
382
123.
521
126.
217
127.
041
127.
077
128.
911
142.
999
163.
415
168.
927
169.
045
180.
472
184.
616
OO
NH
NH
N
OPhPh
CF3
OO
NH
NH
N
OPhPh
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-18
10 9 8 7 6 5 4 3 2 1 ppm
0.99
41.
031
1.05
81.
075
1.09
31.
115
1.13
11.
149
1.22
83.
025
3.04
23.
058
3.07
43.
287
3.30
43.
610
3.62
93.
646
3.66
43.
680
3.69
7
5.16
05.
184
7.47
77.
495
7.51
47.
533
7.57
07.
587
7.60
67.
637
7.65
67.
676
7.69
07.
708
7.96
27.
982
8.15
78.
178
8.53
28.
555
10.0
67
9.52
93.
134
3.04
4
1.17
81.
423
2.03
3
1.12
1
2.12
71.
080
1.99
01.
050
1.03
61.
000
1.01
9
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
7515
.046
26.3
8336
.540
39.3
0439
.512
39.7
2139
.930
40.1
3840
.347
40.5
5742
.742
58.8
06
117.
934
122.
231
124.
239
125.
676
126.
220
126.
614
126.
751
128.
831
133.
667
134.
103
164.
540
169.
161
169.
333
180.
545
185.
046
OO
NH
NH
N
O
Et
Et
OO
NH
NH
N
O
Et
Et
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-19
; -110 9 8 7 6 5 4 3 2 1 0 ppm
0.98
21.
032
1.04
91.
067
1.07
71.
095
1.11
21.
164
1.21
22.
990
3.00
73.
024
3.04
03.
057
3.07
43.
210
3.22
73.
245
3.26
43.
282
3.29
93.
336
3.55
33.
570
3.58
73.
605
3.62
23.
637
3.65
43.
672
5.07
45.
099
7.00
27.
020
7.03
87.
317
7.33
67.
356
7.45
37.
473
8.23
58.
259
9.97
6
9.00
56.
143
1.02
51.
075
1.97
2
1.00
0
0.99
62.
039
1.99
4
0.97
4
0.98
5
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
12.8
5114
.599
25.9
0136
.047
38.8
9439
.103
39.3
1239
.520
39.7
3039
.938
40.1
4642
.304
58.4
35
118.
002
122.
710
129.
374
139.
034
163.
532
168.
219
168.
665
180.
185
183.
499
OO
NH
NH
N
O
Et
Et
OO
NH
NH
N
O
Et
Et
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-20
10 9 8 7 6 5 4 3 2 1 ppm
0.94
71.
016
1.03
31.
052
1.07
21.
089
1.98
62.
499
2.94
12.
958
2.97
52.
992
3.00
93.
027
3.20
83.
226
3.24
53.
263
3.27
93.
543
3.56
03.
579
3.59
63.
614
3.63
13.
647
3.66
43.
998
4.01
74.
034
4.05
25.
000
5.02
55.
755
6.36
76.
389
7.26
87.
287
7.30
67.
373
7.39
17.
401
7.42
17.
905
7.93
08.
516
8.53
8
9.22
46.
376
1.06
31.
179
2.01
7
1.02
6
1.06
8
10.7
99
0.98
7
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
3014
.936
26.3
1636
.374
39.3
0139
.510
39.7
1839
.927
40.1
3540
.344
40.5
5342
.631
58.4
4560
.797
127.
110
127.
307
127.
902
127.
958
129.
220
129.
248
142.
284
142.
623
166.
799
167.
531
169.
271
182.
577
182.
968
OO
NH
NH
N
O
Et
Et Ph
Ph
OO
NH
NH
N
O
Et
Et Ph
Ph
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-21
11 10 9 8 7 6 5 4 3 2 1 ppm
0.80
70.
826
0.84
80.
866
0.98
11.
393
1.40
01.
410
1.41
71.
434
1.45
21.
473
1.49
21.
508
1.52
71.
548
1.56
61.
578
2.84
12.
856
2.86
42.
874
2.88
82.
896
2.91
13.
121
3.13
33.
145
3.15
83.
170
3.46
93.
474
3.49
03.
505
3.62
13.
628
3.64
13.
653
3.66
05.
090
5.11
57.
622
7.64
47.
680
7.70
28.
336
8.36
110
.248
6.35
79.
077
3.99
2
1.01
41.
024
1.02
31.
007
1.06
0
2.01
62.
079
1.01
4
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
11.0
511
.77
20.9
122
.62
26.2
636
.57
39.2
939
.49
39.7
039
.91
40.1
240
.33
40.5
447
.36
50.1
159
.02
118.
4312
0.83
122.
4212
2.74
123.
0512
3.37
123.
5312
6.22
127.
0512
7.09
128.
9214
3.00
163.
3616
9.08
169.
42
180.
5018
4.59
OO
NH
NH
N
O
n-Pr
n-Pr
CF3
OO
NH
NH
N
O
n-Pr
n-Pr
CF3
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-22
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
03
0.
06
8
1.
49
4
2.
58
92
.6
07
2.
62
42
.6
42
2.
65
82
.6
74
2.
69
4
5.
17
3
5.
94
05
.9
79
6.
06
26
.0
76
6.
78
26
.8
01
6.
82
06
.8
40
6.
85
97
.2
60
7.
32
77
.3
49
7.
36
17
.3
70
7.
37
7
3.
22
2
2.
09
7
2.
18
7
1.
00
80
.9
50
1.
00
0
6.
25
9
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
23.8
73
41.2
09
66.4
72
76.8
4377
.161
77.4
78
87.4
30
121.
483
125.
945
128.
367
128.
399
128.
683
135.
843
141.
097
159.
373
165.
488
171.
832
3aaOO
Me
OBn
O
3aaOO
Me
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-23
rac-3aaOO
Me
OBn
O
3aaOO
Me
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-24
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
060.
837
0.85
60.
875
1.74
61.
764
1.78
21.
801
1.81
91.
852
1.87
11.
889
1.90
71.
925
2.61
52.
618
2.63
22.
635
2.65
42.
672
2.67
55.
162
5.92
75.
930
5.93
35.
966
5.96
95.
972
6.09
86.
112
6.76
16.
780
6.80
06.
819
6.83
87.
260
7.29
57.
309
7.31
77.
320
7.32
47.
330
7.33
67.
341
7.35
47.
363
7.36
7
3.16
6
1.10
31.
058
2.04
7
2.12
7
1.00
80.
965
1.00
0
6.10
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
7.72
2
29.7
81
39.7
76
66.4
77
76.8
4277
.160
77.4
78
90.2
04
122.
484
125.
834
128.
382
128.
405
128.
691
135.
864
141.
165
158.
125
165.
519
172.
085
3baOO
Et
OBn
O
3baOO
Et
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-25
rac-3baOO
Et
OBn
O
3baOO
Et
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-26
9 8 7 6 5 4 3 2 1 0 ppm
0.88
70.
906
0.92
41.
234
1.25
21.
265
1.29
11.
695
1.70
81.
724
1.73
71.
792
1.80
51.
822
1.83
42.
630
2.63
32.
645
2.64
82.
651
2.66
42.
668
5.17
05.
927
5.93
05.
933
5.96
65.
969
5.97
26.
083
6.09
86.
765
6.78
46.
803
6.82
36.
842
7.26
07.
307
7.32
17.
327
7.33
17.
337
7.34
37.
348
7.35
37.
361
7.37
07.
374
3.04
2
3.20
4
1.10
81.
032
2.04
1
2.09
7
0.99
30.
964
1.00
0
6.16
4
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.1
0816
.803
38.8
1740
.143
66.4
82
76.8
4477
.162
77.4
80
89.9
65
122.
186
125.
827
128.
382
128.
407
128.
692
135.
862
141.
193
158.
408
165.
539
172.
078
3caOO
n-Pr
OBn
O
3caOO
n-Pr
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-27
rac-3caOO
n-Pr
OBn
O
3caOO
n-Pr
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-28
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
040.
841
0.85
80.
875
1.16
91.
182
1.20
01.
208
1.22
81.
242
1.25
11.
275
1.28
71.
294
1.66
91.
672
1.69
61.
703
1.73
11.
795
1.80
61.
834
2.62
72.
630
2.64
52.
648
2.66
42.
667
5.16
65.
926
5.96
25.
965
6.07
96.
093
6.76
06.
779
6.79
86.
818
6.83
77.
260
7.30
47.
319
7.33
27.
337
7.34
37.
356
7.36
57.
369
3.04
4
6.50
8
1.41
91.
004
2.00
6
2.05
2
0.98
70.
957
1.00
0
6.08
1
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.0
16
22.4
8923
.046
31.7
4436
.721
40.1
48
66.4
80
76.8
4177
.159
77.4
77
89.9
75
122.
217
125.
820
128.
377
128.
407
128.
693
135.
872
141.
205
158.
423
165.
536
172.
087
3daOO
n-Pent
OBn
O
3daOO
n-Pent
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-29
rac-3daOO
n-Pent
OBn
O
3daOO
n-Pent
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-30
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0.0
040.
850
0.86
70.
884
1.16
01.
174
1.23
41.
250
1.28
01.
288
1.29
81.
642
1.69
61.
704
1.71
61.
731
1.79
61.
806
1.83
12.
627
2.63
02.
645
2.66
32.
666
5.16
75.
923
5.92
65.
962
5.96
55.
968
6.08
06.
095
6.76
06.
779
6.79
86.
818
6.83
77.
258
7.30
27.
316
7.32
37.
333
7.33
97.
344
7.35
07.
357
7.36
67.
370
3.06
9
11.2
91
1.15
21.
061
2.08
2
2.09
0
1.02
91.
000
1.05
4
6.43
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.2
0922
.736
23.4
0429
.247
29.4
3129
.628
31.8
9136
.798
40.1
80
66.5
10
76.8
4477
.162
77.4
80
89.9
98
122.
243
125.
845
128.
404
128.
429
128.
714
135.
887
141.
220
158.
426
165.
563
172.
107
3eaOO
n-C8H17
OBn
O
3eaOO
n-C8H17
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-31
rac-3eaOO
n-C8H17
OBn
O
3eaOO
n-C8H17
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-32
10 9 8 7 6 5 4 3 2 1 ppm
0.86
10.
879
0.89
51.
237
1.29
31.
708
1.71
91.
735
1.80
01.
809
1.83
51.
868
2.59
52.
613
2.63
12.
649
2.66
82.
684
2.70
4
5.17
05.
930
5.96
96.
082
6.09
66.
764
6.78
36.
802
6.82
26.
841
7.26
37.
305
7.31
97.
336
7.34
77.
360
3.26
1
20.3
85
1.09
01.
049
2.09
0
2.16
5
1.02
41.
000
1.04
1
6.22
6
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.2
3522
.795
23.4
0129
.444
29.4
7129
.582
29.6
2429
.675
29.7
2632
.016
36.7
9540
.160
66.4
89
76.8
3777
.155
77.4
73
89.9
78
122.
226
125.
828
128.
384
128.
408
128.
696
135.
881
141.
208
158.
409
165.
543
172.
082
3faOO
n-C12H25
OBn
O
3faOO
n-C12H25
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-33
rac-3faOO
n-C12H25
OBn
O
3faOO
n-C12H25
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-34
10 9 8 7 6 5 4 3 2 1 ppm
-0.0
050.
888
0.89
80.
904
0.91
41.
555
1.57
11.
587
1.59
31.
603
1.60
61.
621
1.63
71.
793
1.80
11.
807
1.81
31.
835
2.59
82.
615
2.61
92.
634
2.63
62.
652
2.65
55.
165
5.91
45.
918
5.92
15.
953
5.95
65.
960
6.08
46.
098
6.74
56.
764
6.78
36.
803
6.82
27.
260
7.32
07.
326
7.33
07.
339
7.35
47.
364
7.36
8
6.07
5
2.16
41.
056
2.09
1
2.03
9
1.03
51.
000
1.03
2
6.20
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
23.8
8024
.105
24.2
53
40.9
1345
.362
66.4
68
76.8
4177
.159
77.4
77
90.1
03
122.
075
125.
877
128.
359
128.
399
128.
686
135.
863
141.
159
158.
701
165.
516
172.
070
3gaOO
i-Bu
OBn
O
3gaOO
i-Bu
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-35
rac-3gaOO
i-Bu
OBn
O
3gaOO
i-Bu
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-36
10 9 8 7 6 5 4 3 2 1 ppm
-0.0
00
2.62
12.
640
2.65
72.
676
2.70
12.
720
2.73
72.
757
3.02
33.
058
3.10
73.
142
5.16
85.
928
5.94
15.
977
6.78
46.
803
6.82
26.
842
6.86
17.
122
7.13
97.
234
7.25
57.
275
7.28
37.
297
7.35
5
1.99
5
2.08
6
2.06
7
1.90
4
1.00
02.
022
9.19
3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
39.6
0543
.684
66.4
97
76.8
4477
.162
77.4
80
89.4
10
122.
677
126.
115
127.
531
128.
369
128.
411
128.
604
128.
698
130.
366
133.
906
135.
874
140.
926
157.
784
165.
479
171.
591
3haOO
Bn
OBn
O
3haOO
Bn
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-37
rac-3haOO
Bn
OBn
O
3haOO
Bn
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-38
10 9 8 7 6 5 4 3 2 1 0 ppm
0.00
02.
007
2.02
42.
030
2.03
72.
043
2.05
92.
072
2.14
82.
161
2.17
72.
190
2.21
22.
483
2.49
62.
512
2.52
52.
574
2.58
72.
604
2.61
72.
638
2.67
62.
693
2.71
05.
166
5.93
95.
978
6.11
56.
129
6.77
56.
794
6.81
36.
833
6.85
27.
110
7.12
87.
176
7.19
47.
212
7.25
57.
274
7.29
27.
303
7.31
87.
344
7.35
57.
363
1.19
01.
074
1.07
13.
138
2.13
0
1.00
00.
987
1.00
2
11.3
69
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
29.6
55
38.4
6840
.342
66.5
23
76.8
4677
.164
77.4
81
89.5
24
122.
491
126.
087
126.
496
128.
388
128.
425
128.
704
128.
747
135.
850
140.
404
140.
825
158.
087
165.
462
171.
906
3iaOO
CH2Bn
OBn
O
3iaOO
CH2Bn
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-39
rac-3iaOO
CH2Bn
OBn
O
3iaOO
CH2Bn
OBn
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-40
9 8 7 6 5 4 3 2 1 0 ppm
0.00
01.
479
1.49
81.
509
1.52
81.
539
1.59
41.
612
1.62
51.
642
1.65
31.
702
1.71
31.
736
1.74
71.
766
1.85
41.
865
1.88
52.
577
2.58
52.
593
2.61
02.
630
2.65
25.
165
5.90
65.
945
6.07
06.
084
6.72
96.
748
6.76
86.
787
7.10
97.
127
7.16
27.
179
7.19
77.
247
7.26
47.
278
7.34
37.
349
7.35
97.
367
7.37
5
1.27
71.
775
1.23
81.
108
4.10
5
2.04
5
1.00
00.
970
1.01
03.
139
3.47
75.
171
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
25.1
52
35.6
1236
.170
40.1
27
66.4
94
76.8
3177
.148
77.4
66
89.7
33
122.
373
125.
910
126.
209
128.
390
128.
422
128.
571
128.
694
135.
853
140.
962
141.
268
158.
188
165.
481
171.
933
3jaOO
OBn
OCH2Bn
3jaOO
OBn
OCH2Bn
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-41
rac-3jaOO
OBn
OCH2Bn
3jaOO
OBn
OCH2Bn
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-42
10 9 8 7 6 5 4 3 2 1 ppm
0.00
10.
072
2.87
92.
897
2.91
52.
933
3.00
73.
026
3.04
43.
063
5.14
45.
902
5.94
16.
118
6.13
26.
710
6.72
86.
748
6.76
76.
786
7.26
07.
339
7.34
67.
360
7.37
97.
394
7.41
57.
654
7.66
8
1.07
71.
034
2.00
1
1.03
21.
000
1.03
8
10.1
211.
012
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
42.5
0
66.4
5
76.8
577
.17
77.4
8
90.0
6
121.
1012
5.11
126.
1412
8.32
128.
4012
8.71
128.
8212
9.19
135.
9313
7.97
140.
64
158.
20
165.
47
171.
60
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-43
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-44
10 9 8 7 6 5 4 3 2 1 ppm
0.84
00.
857
0.87
31.
178
1.22
61.
272
1.66
01.
694
1.72
91.
799
1.82
51.
854
2.62
12.
640
2.66
22.
697
3.71
3
5.86
85.
907
6.07
56.
088
6.70
16.
719
6.73
86.
757
6.77
67.
260
7.30
17.
313
3.09
4
12.2
48
1.21
81.
092
2.09
3
3.08
4
1.08
60.
967
1.00
0
1.14
7
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.1
7222
.705
23.3
8329
.217
29.4
0629
.612
31.8
6836
.836
40.0
56
51.7
60
76.8
2877
.146
77.4
64
89.9
83
122.
232
125.
717
140.
811
158.
394
166.
167
172.
090
3ebOO
n-C8H17
OMe
O
3ebOO
n-C8H17
OMe
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-45
r ac-3ebOO
n-C8H17
OMe
O
3ebOO
n-C8H17
OMe
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-46
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
140.
842
0.86
00.
876
1.22
91.
253
1.27
21.
289
1.66
91.
696
1.70
41.
730
1.79
61.
804
1.83
01.
860
2.58
32.
603
2.61
92.
636
2.65
42.
670
2.69
04.
145
4.16
34.
181
4.19
85.
864
5.90
36.
078
6.09
26.
698
6.71
76.
736
6.75
66.
775
7.26
17.
308
7.32
2
3.02
5
15.2
60
1.05
20.
998
2.05
5
2.02
2
1.04
70.
977
1.00
0
0.97
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.1
9414
.319
22.7
2723
.403
29.2
3929
.429
29.6
3031
.888
36.7
9640
.125
60.6
74
76.8
4477
.161
77.4
79
90.0
47
122.
211
126.
192
140.
481
158.
474
165.
789
172.
144
3ecOO
n-C8H17
OEt
O
3ecOO
n-C8H17
OEt
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-47
rac-3ecOO
n-C8H17
OEt
O
3ecOO
n-C8H17
OEt
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-48
10 9 8 7 6 5 4 3 2 1 ppm
-0.0
21
1.24
91.
267
1.28
51.
485
2.57
32.
594
2.60
92.
626
2.64
42.
659
2.67
9
4.14
24.
160
4.17
74.
195
5.87
05.
910
6.05
06.
064
6.71
26.
731
6.75
16.
770
6.78
97.
260
7.37
07.
384
3.04
53.
099
2.07
0
2.07
2
1.02
90.
990
1.00
0
1.03
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.3
04
23.8
89
41.2
08
60.6
76
76.8
4277
.160
77.4
78
87.5
06
121.
491
126.
321
140.
374
159.
417
165.
750
171.
895
3acOO
Me
OEt
O
3acOO
Me
OEt
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-49
rac-3acOO
Me
OEt
O
3acOO
Me
OEt
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-50
-2-110 9 8 7 6 5 4 3 2 1 0 ppm
-0.0
190.
837
0.85
50.
870
0.91
30.
929
1.17
31.
224
1.25
21.
268
1.66
81.
703
1.72
91.
792
1.80
11.
826
1.85
61.
888
1.90
51.
921
1.93
81.
955
1.97
11.
988
2.58
32.
602
2.61
92.
638
2.65
72.
673
2.69
33.
884
3.90
15.
879
5.91
86.
074
6.08
86.
697
6.71
66.
736
6.75
56.
774
7.26
07.
309
7.32
3
3.08
96.
061
12.0
821.
177
1.07
31.
059
2.06
2
2.07
4
1.02
71.
000
1.02
2
1.01
3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.1
8219
.195
22.7
0923
.384
27.8
1329
.222
29.4
0429
.609
31.8
7136
.773
40.0
76
70.7
7476
.837
77.1
5577
.472
90.0
35
122.
171
126.
133
140.
470
158.
487
165.
845
172.
131
3edOO
n-C8H17
Oi-Bu
O
3edOO
n-C8H17
Oi-Bu
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-51
3edOO
n-C8H17
Oi-Bu
O
3edOO
n-C8H17
Oi-Bu
O
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-52
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0.0
08
1.45
82.
007
2.46
72.
485
2.50
32.
522
2.69
02.
709
2.72
62.
745
5.12
05.
152
5.18
55.
761
5.92
05.
959
6.71
06.
729
6.74
86.
768
6.78
77.
260
7.30
07.
313
7.31
67.
347
3.05
9
3.07
5
1.18
31.
046
2.09
3
1.01
31.
023
1.00
0
5.04
5
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
13.2
11
23.5
07
39.6
89
66.4
40
76.8
4677
.163
77.4
81
88.1
02
117.
337
125.
643
128.
353
128.
677
135.
886
140.
942
165.
482
170.
924
171.
567
3laOO
Me
OBn
OMe
3laOO
Me
OBn
OMe
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-53
rac-3laOO
Me
OBn
OMe
3laOO
Me
OBn
OMe
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-54
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.96
50.
977
0.99
01.
440
1.95
01.
966
1.98
21.
998
2.01
52.
032
2.06
92.
085
2.44
62.
465
2.48
32.
501
2.67
92.
697
2.71
52.
734
5.14
9
5.76
05.
909
5.94
86.
705
6.72
46.
743
6.76
36.
781
7.26
07.
310
7.34
17.
379
6.08
5
3.09
3
1.01
32.
066
1.06
11.
029
2.01
1
1.05
81.
023
1.00
0
5.06
4
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
22.6
8423
.682
26.3
80
36.4
8039
.898
66.3
95
76.8
4277
.160
77.4
78
88.2
04
115.
931
125.
642
128.
310
128.
342
128.
653
135.
901
141.
012
165.
440
171.
799
174.
571
3maOO
Me
OBn
Oi-Bu
3maOO
Me
OBn
Oi-Bu
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-55
rac-3maOO
Me
OBn
Oi-Bu
3maOO
Me
OBn
Oi-Bu
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-56
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0.0
020.
070
1.74
4
2.75
22.
770
2.78
92.
807
2.90
32.
923
2.94
02.
960
5.13
4
5.85
85.
897
6.26
96.
728
6.74
76.
766
6.78
56.
804
7.25
97.
297
7.33
57.
352
7.37
57.
480
7.49
2
3.02
1
1.16
11.
042
2.04
2
1.03
0
1.00
7
1.00
0
5.24
05.
399
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
25.2
76
41.1
49
66.4
13
76.8
4177
.476
88.2
01
116.
375
125.
902
127.
555
128.
326
128.
366
128.
683
129.
444
130.
091
131.
228
135.
936
140.
861
165.
501
169.
985
170.
961
3naOO
Me
OBn
OPh
3naOO
Me
OBn
OPh
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-57
rac-3naOO
Me
OBn
OPh
3naOO
Me
OBn
OPh
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-58
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0.0
071.
313
1.32
81.
338
1.34
81.
361
1.37
01.
381
1.39
01.
409
1.42
61.
458
1.48
11.
506
1.67
51.
837
2.07
62.
091
2.14
82.
182
2.19
42.
213
2.32
12.
344
2.54
62.
563
2.58
32.
600
2.72
82.
749
2.76
52.
787
2.82
72.
831
5.15
65.
732
5.92
95.
968
6.74
06.
758
6.77
86.
797
6.81
67.
260
7.31
97.
354
7.38
8
1.03
41.
170
1.07
11.
012
1.05
71.
033
0.99
41.
036
2.05
3
2.01
8
0.99
01.
000
1.00
1
5.14
6
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
22.3
9527
.507
27.5
4636
.972
38.4
00
66.4
47
76.8
4077
.158
77.4
76
87.1
35
113.
786
125.
649
128.
394
128.
690
135.
898
141.
085
165.
533
172.
071
173.
785
OO OBn
O
3oa
OO OBn
O
3oa
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-59
OO OBn
O
rac-3oa
OO OBn
O
3oa
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013
Kumar & Mukherjee, SI-Part-B, Page S-60
10 9 8 7 6 5 4 3 2 1 ppm
-0.0
06
1.60
2
2.73
12.
771
2.94
72.
987
6.07
96.
093
7.25
97.
666
7.68
0
3.02
8
1.06
61.
096
1.00
0
0.98
8
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
23.9
92
43.0
92
76.8
4177
.159
77.4
7685
.702
121.
005
159.
646
172.
111
173.
664
OO
Me
O
OH
(S)-(+)-4-methylmuconolactone
OO
Me
O
OH
(S)-(+)-4-methylmuconolactone
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2013