Assembly of Enantioenriched cis-3a,8a-Hexahydropyrrolo[2,3-b]indole Scaffolds by Silver(I)-Catalyzed Asymmetric Domino Reaction of Isocyanoacetates in the Presence of Cinchona-Derived Chiral Phosphorus Ligands

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• 作者：Hengguang Cheng ; Runmei Zhang ; Shiwei Yang ; Min Wang ; Xiaofei Zeng ; Lingjie Xie ; Chunsong Xie ; Jing Wu and Guofu Zhong
• 关键词：cycloaddition ; domino reaction ; hexahydropyrrolo[2 ; 3-b]indoles ; isocyanoacetates
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：March 17, 2016
• 年：2016
• 卷：358
• 期：6
• 页码：970-976
• 全文大小：496K
• ISSN：1615-4169

文摘

By using Cinchona-derived chiral phosphines as catalytic ligands, enantioenriched cis-3a,8a-hexahydropyrrolo[2,3-b]indoles (ent-HPIs), which are core scaffolds in a large array of biologically active natural products, can be convergently assembled under mild conditions through the silver(I)-catalyzed asymmetric domino reaction of readily available isocyanoacetates and 2-(2-aminophenyl)acrylates. Various functionalities can be tolerated in the reaction, affording enantioenriched HPIs in high overall yields and good enantioselectivities (up to 92% ees).