Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones

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• 作者：Zhan-Ming Zhang ; Bing Xu ; Shan Xu ; Prof. Dr. Hai-Hong Wu and Prof. Dr. Junliang Zhang
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：May 17, 2016
• 年：2016
• 卷：128
• 期：21
• 页码：6432-6436
• 全文大小：1028K
• ISSN：1521-3757

文摘

Reported herein is an asymmetric [3+2] cycloaddition reaction of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones, a reaction which is enabled by a Ming-Phos-derived copper(I) catalyst (Ming-Phos=chiral sulfinamide monophosphines, Figure 1). This method provides scalable and efficient access to the highly substituted pyrrolidines with a trifluoromethylated, all-carbon quaternary stereocenter in good yields with up to greater than 20:1 d.r. and 98 % ee. The reaction has a broad substrate scope and tolerates a wide range of functional groups.