Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

J Am Chem Soc. 2014 Jan 8;136(1):76-9. doi: 10.1021/ja410932t. Epub 2013 Dec 17.

Abstract

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

Publication types

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

MeSH terms

  • Acylation
  • Alcohols / chemistry
  • Alkenes / chemistry*
  • Catalysis
  • Computer Simulation*
  • Heterocyclic Compounds / chemistry*
  • Hydroxylation
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Models, Chemical*
  • Organophosphonates / chemistry*

Substances

  • Alcohols
  • Alkenes
  • Heterocyclic Compounds
  • Organophosphonates
  • carbene
  • Methane