An organocatalytic Michael-cyclization cascade of 4-oxa-α,β-unsaturated carboxylic acids with aldehydes: facile synthesis of chiral γ-lactols and trisubstituted γ-lactones

Chem Commun (Camb). 2015 Feb 28;51(17):3596-9. doi: 10.1039/c4cc09686j.

Abstract

An organocatalytic Michael-cyclization cascade of aldehydes with 4-oxa-α,β-unsaturated carboxylic acids has been developed, giving functionalized γ-lactols with high yields and enantioselectivities. The products could be easily transformed into complex trisubstituted γ-lactones and γ-lactams.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Cyclization
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Amines
  • Carboxylic Acids
  • Lactones