Stereocontrolled Synthesis of Trisubstituted Cyclopropanes: Expedient, Atom-Economical, Asymmetric Syntheses of (+)-Bicifadine and DOV21947

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• 作者：Feng Xu ; Jerry A. Murry ; Bryon Simmons ; Edward Corley ; Kenneth Fitch ; Sandor Karady ; David Tschaen
• 刊名：Organic Letters
• 出版年：2006
• 出版时间：August 17, 2006
• 年：2006
• 卷：8
• 期：17
• 页码：3885 - 3888
• 全文大小：78K
• 年卷期：v.8,no.17(August 17, 2006)
• ISSN：1523-7052

文摘

An expedient, atom-economical, asymmetric synthesis of 1-aryl-3-azabicyclo[3.1.0]hexanes, including (+)-Bicifadine and DOV21947, in a single-stage through process without isolation of any intermediates has been developed. The key of this synthesis is the in-depth mechanisticunderstanding of the complicated epoxy nitrile coupling at each reaction stage. Therefore, the desired trisubstituted cyclopropane can beprepared in high ee and yield by controlling the reaction pathway through manipulating the nitrile anion aggregation state.