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JJ Clemens, JL Asgian, BB Busch, T Coon, J Ernst, L Kaljevic, PJ Krenitsky, TD Neubert, EJ Schweiger, A Termin and D Stamos
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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Concepts
Aldol condensation, Functional groups, Enantiomer, Racemic mixture, Stereochemistry
MeSH headings
-
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