Organocatalytic direct asymmetric vinylogous Michael reaction of an α,β-unsaturated γ-butyrolactam with enones

J Org Chem. 2011 Mar 4;76(5):1472-4. doi: 10.1021/jo102223v. Epub 2011 Jan 18.

Abstract

An organocatalytic asymmetric direct vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to enones has been achieved with a simple bifunctional thiourea-tertiary amine catalyst, affording the γ-substituted butyrolactam products with high diastereo- and enantioselectivity (up to >40:1 dr and 94-99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Lactams / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • Amines
  • Ketones
  • Lactams
  • Thiourea