Regiodivergent Intermolecular [3+2] Cycloadditions of Vinyl Aziridines and Allenes: Stereospecific Synthesis of Chiral Pyrrolidines

被引：58

作者：

Lin, Tao-Yan ^{[1
]}

Zhu, Chao-Ze ^{[1
]}

Zhang, Peichao ^{[1
]}

Wang, Yidong ^{[1
]}

Wu, Hai-Hong ^{[1
]}

Feng, Jian-Jun ^{[1
]}

Zhang, Junliang ^{[1
,2
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 36期

关键词：

cycloaddition; allenes; chirality; heterocycles; rhodium; INTRAMOLECULAR HYDROAMINATION; RING EXPANSIONS; ASYMMETRIC-SYNTHESIS; DIVERGENT SYNTHESIS; DIAZO-COMPOUNDS; ACID; HETEROCYCLES; ALLENAMIDES; ISOCYANATES; REARRANGEMENT;

D O I：

10.1002/anie.201605530

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：10844 / 10848

页数：5

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