Diastereoselective One-Pot Knoevenagel Condensation/Corey鈥揅haykovsky Cyclopropanation

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• 作者：Jeremy J. Clemens ; Juliana L. Asgian ; Brett B. Busch ; Timothy Coon ; Justin Ernst ; Leonard Kaljevic ; Paul J. Krenitsky ; Timothy D. Neubert ; Edwin J. Schweiger ; Andreas Termin ; Dean Stamos
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：January 18, 2013
• 年：2013
• 卷：78
• 期：2
• 页码：780-785
• 全文大小：262K
• 年卷期：v.78,no.2(January 18, 2013)
• ISSN：1520-6904

文摘

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鈥揅haykovsky 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 (卤)-bicifadine in two steps is provided to demonstrate the utility of the method.