Diastereoselective one-pot Knoevenagel condensation/Corey-Chaykovsky cyclopropanation

Autor: Timothy Neubert, Timothy Coon, Brett B. Busch, Justin T. Ernst, Paul Krenitsky, Leonard Kaljevic, Edwin Schweiger, Andreas Termin, Jeremy J. Clemens, Dean Stamos, Juliana L. Asgian
Rok vydání: 2012
Předmět:
Zdroj: The Journal of organic chemistry. 78(2)
ISSN: 1520-6904
Popis: 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.
Databáze: OpenAIRE