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TRANSCRIPT
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Catalytic enantioselective synthesis of cyclopropanes featuring vicinal all-carbon quaternary stereocenters with a CH2F group; study of influence of C-F···H-N
interactions on reactivity
Zhong-Yan Cao,‡a Wenmin Wang,‡b Kui Liao,a Xiaoming Wang,d Jian Zhou*a,c,d and Jing Ma*b
aShanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. China. E-mail: [email protected]. bInstitute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P R China. E-mail: [email protected]. cShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. China. dState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China. ‡These authors contributed equally to this article.
Supporting Information (Part C)
HPLC Spectra of 3a-3q, 4, 7a-7e 2-24
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2018
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NNHH
OOCHCH22FF
nnBuBu
3a3a
NNHH
OOCCHH22FF
nnBBuu
33aa
3
NNHH
OOCCHH22FF
nnBBuu
MMee
33bb
NNHH
OOCHCH22FF
nnBuBu
MeMe
3b3b
4
NNHH
OOCCHH22FF
nnBBuu
FF
33cc
NNHH
OOCHCH22FF
nnBuBu
FF
3c3c
5
NNHH
OOCCHH22FF
nnBBuu
CCll
33dd
NNHH
OOCHCH22FF
nnBuBu
ClCl
3d3d
6
NNHH
OOCCHH22FF
nnBBuu
BBrr
33ee
NNHH
OOCHCH22FF
nnBuBu
BrBr
3e3e
7
NNHH
OOCCHH22FF
nnBBuu
II
33ff
NNHH
OOCHCH22FF
nnBuBu
II
3f3f
8
NNHH
OOCCHH22FF
nnBBuu
MMee33gg
NNHH
OOCHCH22FF
nnBuBu
MeMe3g3g
9
NNHH
OOCCHH22FF
nnBBuu
MMeeMMee
33hh
NNHH
OOCHCH22FF
nnBuBu
MeMeMeMe
3h3h
10
NNHH
OOCCHH22FF
CCll
CCll
33ii
NNHH
OOCHCH22FF
ClCl
ClCl
3i3i
11
NNHH
OOCCHH22FF
BBrr
CCll
33jj
NNHH
OOCHCH22FF
BrBr
ClCl
3j3j
12
NNHH
OOCCHH22FFCCll
MMee
33kk
NNHH
OOCHCH22FFClCl
MeMe
3k3k
13
NNHH
OOCCHH22FFCCll
33ll
NNHH
OOCHCH22FFClCl
3l3l
14
NNHH
OOCCHHFF22
nnBBuu
CCll
33mm
NNHH
OOCHFCHF22
nnBuBu
ClCl
3m3m
15
NNHH
OOCCHHFF22
nnBBuu
BBrr
33nn
NNHH
OOCHFCHF22
nnBuBu
BrBr
3n3n
16
NNHH
OOCCHHFF22
nnBBuu
II
33oo
NNHH
OOCHFCHF22
nnBuBu
II
3o3o
17
NNHH
OOCCHHFF22
OOMMee
BBrr
33pp
NNHH
OOCHFCHF22
OMeOMe
BrBr
3p3p
18
NNOOCCHH22FF
nnBBuu
MMee33qq
NNOOCHCH22FF
nnBuBu
MeMe3q3q
19
NNOO
CHCH22FF
nnBuBu
OO22SS NONO22
44
NNOO
CHCH22FF
nnBuBu
OO22SS NONO22
44
20
FFHH22CC CCOOOOMMee
PPMMPP
nnBBuu
77aa
FHFH22CC COOMeCOOMe
PMPPMP
nnBuBu
7a7a
21
FFHH22CC CCOOOOMMee
pp--BBrrCC66HH44
nnBBuu
77bb
FHFH22CC COOMeCOOMe
pp-BrC-BrC 66HH44
nnBuBu
7b7b
22
FFHH22CC CCOOOOMMee
mm--BBrrCC66HH44
nnBBuu
77cc
FHFH22CC COOMeCOOMe
mm-BrC-BrC66HH44
nnBuBu
7c7c
23
FFHH22CC CCOOOOMMee
pp--BBrrCC66HH44
77dd
FHFH22CC COOMeCOOMe
pp-BrC-BrC 66HH44
7d7d
24
FF22HHCC CCOOOOMMee
pp--BBrrCC66HH44
77ee
FF22HCHC COOMeCOOMe
pp-BrC-BrC 66HH44
7e7e