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The Journal of organic chemistry

Diastereoselective one-pot Knoevenagel condensation/Corey-Chaykovsky cyclopropanation.


PMID 23252964

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.

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295183
Cyclopropane, ≥99%
C3H6