1. Diastereoselective one-pot Knoevenagel condensation/Corey-Chaykovsky cyclopropanation
- Author
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Timothy Neubert, Timothy Coon, Brett B. Busch, Justin T. Ernst, Paul Krenitsky, Leonard Kaljevic, Edwin Schweiger, Andreas Termin, Jeremy J. Clemens, Dean Stamos, and Juliana L. Asgian
- Subjects
Cyclopropanes ,Aldehydes ,Acetonitriles ,Molecular Structure ,Cyclopropanation ,Aryl ,Organic Chemistry ,Stereoisomerism ,Ring (chemistry) ,Cyclopropane ,chemistry.chemical_compound ,chemistry ,Nitriles ,Organic chemistry ,Racemic mixture ,Knoevenagel condensation ,Enantiomer - 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.
- Published
- 2012