Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols

Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols

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′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereos...

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Bibliographic Details
Main Authors: Davies, S, Key, MS, Rodriguez-Solla, H, Sanganee, H, Savory, E, Smith, A
Format: Journal article
Language:English
Published: 2003
Description
Summary: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′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ S N1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive cleavage of the isolated 1′-acyloxy-2′-hydroxy derivatives generates 1,2-diols in high yields and in high ee.

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