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铑(II)/钯(0)双催化:类卡宾N-H插入/烯丙基化串联反应构建高度官能化和多取代的吡咯烷

Rh(II)/Pd(0) Dual Catalysis: Carbenoid N-H Insertion/Allylation Cascade Reaction to Construct Highly Functionalized and Polysubstituted Pyrrolidines.

作者信息

Tang Maocheng, Jiao Xianyan, He Deping, Zhao Ji-Xing, Liu Ping, Li Chun-Tian

机构信息

State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engneering, Shihezi University, Shihezi 832003, China.

Analysis and Testing Center, Shihezi University, Shihezi 832003, China.

出版信息

Molecules. 2024 Dec 13;29(24):5880. doi: 10.3390/molecules29245880.

Abstract

In the category of drugs approved by the U.S. FDA, pyrrolidine is the most frequently used core of five-membered nonaromatic heterocycles containing nitrogen. Herein, a Rh(II)/Pd(0) dual-catalyzed carbenoid N-H insertion/allylation cascade reaction has been developed. This protocol provide an efficient approach for the construction of diverse highly functionalized and polysubstituted pyrrolidines in high yields (up to 91%) with excellent chemoselectivities and high diastereoselectivities (>20:1) under mild reaction conditions.

摘要

在美国食品药品监督管理局(FDA)批准的药物类别中,吡咯烷是含氮五元非芳香杂环中最常用的核心结构。在此,已开发出一种铑(II)/钯(0)双催化类卡宾N-H插入/烯丙基化串联反应。该方法提供了一种有效的途径,可在温和的反应条件下,以高产率(高达91%)、优异的化学选择性和高非对映选择性(>20:1)构建多种高度官能化和多取代的吡咯烷。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfa0/11676634/47899e7875c7/molecules-29-05880-g001.jpg

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