Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

Chem Commun (Camb). 2013 Oct 18;49(81):9329-31. doi: 10.1039/c3cc44059a.

Abstract

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl-isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25 : 1 dr and 96% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Isoxazoles / chemistry
  • Ketones / chemistry
  • Lactams / chemistry*
  • Molecular Conformation
  • Quinine / chemistry
  • Stereoisomerism

Substances

  • Amides
  • Isoxazoles
  • Ketones
  • Lactams
  • Quinine