Diastereoselective one-pot Knoevenagel condensation/Corey-Chaykovsky cyclopropanation

J Org Chem. 2013 Jan 18;78(2):780-5. doi: 10.1021/jo302443k. Epub 2012 Dec 31.

Abstract

Efforts to substitute the cyclopropane ring in a series of aryl cyclopropylnitriles led to the discovery of an operationally simple one-pot method for Knoevenagel condensation and subsequent Corey-Chaykovsky cyclopropanation giving diastereomerically pure products as a racemic mixture of enantiomers. Method development and results for variably substituted aryl acetonitriles and aldehydes in the reaction are reported. A concise synthesis of (±)-bicifadine in two steps is provided to demonstrate the utility of the method.

MeSH terms

  • Aldehydes / chemistry*
  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Cyclopropanes
  • Nitriles
  • cyclopropane