Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals

Philip A. Woods, Louis C. Morrill, Tomas Lebl, Alexandra M. Z. Slawin, Ryan A. Bragg, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acy1-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

Original languageEnglish
Pages (from-to)2660-2663
Number of pages4
JournalOrganic Letters
Volume12
Issue number11
DOIs
Publication statusPublished - 4 Jun 2010

Keywords

  • BETA,BETA-DISUBSTITUTED GAMMA-BUTYROLACTONES
  • CATALYTIC ENANTIOSELECTIVE SYNTHESIS
  • CARBON QUATERNARY STEREOCENTERS
  • ASYMMETRIC-SYNTHESIS
  • 1,3-DICARBONYL COMPOUNDS
  • METHYL CYANOFORMATE
  • BETA-KETOESTERS
  • ACYL TRANSFER
  • O-CARBOXYL
  • CONSTRUCTION

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