Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones

Org Lett. 2009 Oct 1;11(19):4298-301. doi: 10.1021/ol901586t.

Abstract

The organocatalytic transfer hydrogenation reactions of 3-phenyl-2-cyclopentenone with imidazolidinone catalysts are evaluated using the hybrid density functional (B3LYP/6-31G(d)) theory. The origin of the preference for the (E) iminium transition state is determined, and the stereoselectivity of hydride transfer is investigated.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Computer Simulation
  • Cyclopentanes / chemistry
  • Hydrogenation
  • Imidazolidines / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Models, Chemical
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Cyclopentanes
  • Imidazolidines
  • Ketones