The Journal of organic chemistry | 21 Dec 2012
JJ Clemens, JL Asgian, BB Busch, T Coon, J Ernst, L Kaljevic, PJ Krenitsky, TD Neubert, EJ Schweiger, A Termin and D Stamos
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.
* Data courtesy of Altmetric.com