Asymmetric conjugate hydrocyanation of α,β-unsaturated N-acylpyrroles with the Ru(phgly)2(binap)-CH3OLi catalyst system

Org Lett. 2014 Feb 7;16(3):808-11. doi: 10.1021/ol403545b. Epub 2014 Jan 9.

Abstract

Asymmetric conjugate hydrocyanation of α,β-unsaturated carboxylic acid derivatives catalyzed by a Ru[(S)-phgly]2[(S)-binap]-CH3OLi system was examined. The N-acylpyrrole gave the best result in terms of reactivity and enantioselectivity. A series of substrates with alkyl or heterosubstituted alkyl groups at the β-position reacted with a substrate-to-catalyst molar ratio of 200-2000 to afford the β-cyano products in the range of 88%->99% ee. The mode of enantioselection in the hydrocyanation was proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Lithium / chemistry*
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Nitriles / chemistry*
  • Pyrroles / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Coordination Complexes
  • Naphthalenes
  • Nitriles
  • Pyrroles
  • Ruthenium
  • Lithium