Highly Substituted Enantioenriched Cyclopentane Derivatives by Palladium-Catalyzed [3 + 2] Trimethylenemethane Cycloadditions with Disubstituted Nitroalkenes

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• 作者：Barry M. Trost ; Dustin A. Bringley ; B. Michael O鈥橩eefe
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：November 15, 2013
• 年：2013
• 卷：15
• 期：22
• 页码：5630-5633
• 全文大小：288K
• 年卷期：v.15,no.22(November 15, 2013)
• ISSN：1523-7052

文摘

尾,尾-Disubstituted nitroalkenes readily undergo palladium-catalyzed [3 + 2] cycloaddition with trimethylenemethane to generate nitrocyclopentanes in excellent yield and enantioselectivity. The reaction provides access to heavily substituted cyclopentanes containing up to three contiguous stereocenters, and the products may be converted to both cyclopentylamines and cyclopentenones. A rare dependence of the sense of chirality of the cycloadducts was observed to be exclusively dependent on the structure of the palladium-bound trimethylenemethane intermediate.