Asymmetric vinylogous Michael reaction of alpha,beta-unsaturated ketones with gamma-butenolide under multifunctional catalysis

Chem Commun (Camb). 2010 Aug 28;46(32):5957-9. doi: 10.1039/c0cc01054e. Epub 2010 Jul 2.

Abstract

A general and direct organocatalytic asymmetric vinylogous Michael reaction of gamma-butenolide with alpha,beta-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile gamma-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30:1 dr and 95-99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • Amines / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Ketones / chemistry*
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Amines
  • Ketones
  • butenolide
  • 4-Butyrolactone