Bifunctional 3,3'-Ph2-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

Org Lett. 2011 Dec 16;13(24):6410-3. doi: 10.1021/ol202713f. Epub 2011 Nov 16.

Abstract

Bifunctional 3,3'-Ph(2)-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam has been developed. The catalytic activity of this protocol was slightly affected by different types of Michael acceptors, such as a variety of enones as well as α,β-unsaturated N-acylpyrroles. The Michael products were obtained with high diastereoselectivities (up to 20:1) and excellent enantioselectivities (up to 98%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / chemistry*
  • Catalysis
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Magnesium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Stereoisomerism

Substances

  • Ketones
  • Organometallic Compounds
  • Pyrroles
  • Magnesium
  • 4-Butyrolactone