Organic letters

One-carbon homologation of N-sulfonylaziridines to allylic amines using dimethylsulfonium methylide

DM Hodgson, MJ Fleming, SJ Stanway

Index: Hodgson, David M.; Fleming, Matthew J.; Stanway, Steven J. Organic Letters, 2005 , vol. 7, # 15 p. 3295 - 3298

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Citation Number: 24

Abstract

Regio- and stereodefined allylic N-sulfonylamines are synthesized in high yields and under experimentally straightforward conditions by reaction of N-sulfonylaziridines with excess dimethylsulfonium methylide. ... During that study, it was observed that reaction of excess (4 equiv) dimethylsulfonium methylide 2 9 with trans-aziridines 1 (R = Ph; Ar = Ph, p-ClC 6 H 4 ) gave allylic amines 4 (Scheme 1); the corresponding cis-2,3-diphenyl-substituted and trans-2,3-dimethyl-substituted ...