γ′-Selective Functionalization of Cyclic Enones: Construction of a Chiral Quaternary Carbon Center by [4+2] Cycloaddition/Retro-Mannich Reaction with 3-Substituted Maleimides

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• 作者：Chuncheng Zou ; Chuikun Zeng ; Prof. Dr. Zhen Liu ; Min Lu ; Xiaohua Sun and Prof. Dr. Jinxing Ye
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：November 7, 2016
• 年：2016
• 卷：128
• 期：46
• 页码：14469-14473
• 全文大小：885K
• ISSN：1521-3757

文摘

The first example of organocatalyzed γ′-selective functionalization of cyclic enones with 3-substituted maleimides results in the stereoselective construction quaternary carbon center is presented. The reactions provided γ′-functionalized cyclic enones and β-functionalized cyclopentenones in good to excellent yields with excellent diastereo- and enantioselectivities. DFT calculations indicated that the reaction might proceed as a [4+2] cycloaddition/retro-Mannich reaction which could explain the unexpected product with a chiral quaternary carbon center and the excellent stereoselectivity.