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

Stephen G. Davies*, Min Suk Key, Humberto Rodriguez-Solla, Hitesh J. Sanganee, Edward D. Savory, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

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′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ SN1 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.

Original languageEnglish
Pages (from-to)1659-1662
Number of pages4
JournalSynlett
Issue number11
DOIs
Publication statusPublished - 1 Jan 2003

Keywords

  • Asymmetric synthesis
  • Homochiral 1,2-diols
  • SuperQuat enamides

Fingerprint

Dive into the research topics of 'Oxidative functionalisation of superquat enamides: Asymmetric synthesis of homochiral 1,2 diols'. Together they form a unique fingerprint.

Cite this