Regiodivergent Intermolecular [3+2] Cycloadditions of Vinyl Aziridines and Allenes: Stereospecific Synthesis of Chiral Pyrrolidines
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- 作者：Tao-Yan Lin ; Chao-Ze Zhu ; Peichao Zhang ; Yidong Wang ; Prof. Dr. Hai-Hong Wu ; Dr. Jian-Jun Feng and Prof. Dr. Junliang Zhang
- 刊名：Angewandte Chemie
- 出版年：2016
- 出版时间：August 26, 2016
- 年：2016
- 卷：128
- 期：36
- 页码：11002-11006
- 全文大小：946K
- ISSN：1521-3757
文摘
The first rhodium-catalyzed intermolecular [3+2] cycloaddition reaction of vinyl aziridines and allenes for the synthesis of enantioenriched functionalized pyrrolidines was realized. [3+2] cycloaddition with the proximal C=C bond of N-allenamides gave 3-methylene-pyrrolidines in high regio- and diastereoselectivity, whereas, 2-methylene-pyrrolidines were obtained as the major products by the cycloadditions of vinyl aziridines with the distal C=C bond of allenes. Use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile functionalization of the cycloadducts make this approach very practical and attractive.