Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes

J Am Chem Soc. 2004 Jan 14;126(1):14-5. doi: 10.1021/ja0391208.

Abstract

Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted beta-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Cyclization
  • Hydrocarbons, Brominated / chemistry*
  • Ketones / chemistry
  • Lactones / chemical synthesis*
  • Models, Molecular

Substances

  • Aldehydes
  • Hydrocarbons, Brominated
  • Ketones
  • Lactones