Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis

VK Aggarwal*, CL Winn

*Corresponding author for this work

Research output: Contribution to journalReview article (Academic Journal)peer-review

Abstract

The reaction of sulfur ylides with carbonyl compounds to give epoxides is an important synthetic method. This Account charts the recent advances in rendering this process both asymmetric and catalytic. Two catalytic methods have been developed: the first involving the reaction of a sulfide with an alkyl halide in the presence of a base and aldehyde and the second involving the reaction of a sulfide with a diazo compound or diazo precursor in the presence of a metal catalyst and aldehyde. These catalytic methods coupled with suitable chiral sulfides provide a new catalytic asymmetric epoxidation process for the preparation of epoxides. The scope of the two catalytic processes is discussed together with the factors that influence both relative and absolute stereo chemistry. The application of these methods in target-orientated synthesis is also reviewed.

Original languageEnglish
Pages (from-to)611-620
Number of pages10
JournalAccounts of Chemical Research
Volume37
Issue number8
DOIs
Publication statusPublished - Aug 2004

Keywords

  • IN-SITU GENERATION
  • OPTICALLY-ACTIVE EPOXIDES
  • CHIRAL SULFIDES
  • SULFONIUM YLIDES
  • DIAZO-COMPOUNDS
  • ALDEHYDES
  • AZIRIDINATION
  • CYCLE
  • CYCLOPROPANATION
  • TOSYLHYDRAZONE

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