cheminform abstract: vinyl diazophosphonates as precursors to quaternary substituted indolines and...

ChemInform 2011, 42, issue 01 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Organo-phosphorus compounds S 0080 DOI: 10.1002/chin.201122195 Vinyl Diazophosphonates as Precursors to Quaternary Substituted Indolines and Cyclopentenes. — Vinyl diazophosphonates (IV), exclusively synthesized as (E)-iso- mers, undergo a sulfonium ylide rearrangement [cf. (VI)] or an intramolecular C—H insertion reaction [cf. (IX)]. Optically active substrates react with retention of config- uration [cf.(XI)]. The mixture of cis- and trans-phosphonates obtained from substrates (XII) is converted into the trans-diastereomers by simply subjecting the mixture to DBU. — (WANG, J.; BOYARSKIKH, V.; RAINIER*, J. D.; Org. Lett. 13 (2011) 4, 700-702, http://dx.doi.org/10.1021/ol102931n ; Dep. Chem., Univ. Utah, Salt Lake City, UT 84112, USA; Eng.) — H. Simon 22- 195

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Page 1: ChemInform Abstract: Vinyl Diazophosphonates as Precursors to Quaternary Substituted Indolines and Cyclopentenes

Organo-phosphorus compoundsS 0080 DOI: 10.1002/chin.201122195

Vinyl Diazophosphonates as Precursors to Quaternary Substituted Indolines and Cyclopentenes. — Vinyl diazophosphonates (IV), exclusively synthesized as (E)-iso-mers, undergo a sulfonium ylide rearrangement [cf. (VI)] or an intramolecular C—H insertion reaction [cf. (IX)]. Optically active substrates react with retention of config-uration [cf.(XI)]. The mixture of cis- and trans-phosphonates obtained from substrates (XII) is converted into the trans-diastereomers by simply subjecting the mixture to DBU. — (WANG, J.; BOYARSKIKH, V.; RAINIER*, J. D.; Org. Lett. 13 (2011) 4, 700-702, http://dx.doi.org/10.1021/ol102931n ; Dep. Chem., Univ. Utah, Salt Lake City, UT 84112, USA; Eng.) — H. Simon

22- 195

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