Oxidative functionalisation of superquat enamides: asymmetric synthesis of homochiral 1, 2 diols

SG Davies, MS Key, H Rodriguez-Solla, HJ Sanganee…

Index: Davies, Stephen G.; Key, Min-Suk; Rodriguez-Solla, Humberto; Sanganee, Hitesh J.; Savory, Edward D.; Smith, Andrew D. Synlett, 2003 , # 11 p. 1659 - 1662

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Citation Number: 15

Abstract

Abstract Homochiral (E)-enamides derived from (S)-4-phenyl-5, 5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′ R, 2′ S)- 1′-acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ SN 1 type epoxide ...