Rhodium( I)-Catalyzed Intermolecular Aza-[4+3] Cycloaddition of Vinyl Aziridines and Dienes: Atom-Economical Synthesis of Enantiomerically Enriched Functionalized Azepines

被引：87
|
作者：
Zhu, Chao-Ze [1 ]
Feng, Jian-Jun [1 ]
Zhang, Junliang [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 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 | 2017年 / 56卷 / 05期
关键词：
4+3] cycloaddition; chiral azepines; chirality transfer; dienes; vinyl aziridines; FORMAL 3+2+2 CYCLOADDITION; MEDIUM-SIZED RINGS; ENANTIOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; NITROGEN-HETEROCYCLES; DIVERGENT SYNTHESIS; FACILE SYNTHESIS; ALKYNES; DERIVATIVES; ANNULATION;
D O I：
10.1002/anie.201609608
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new synthetic application of vinyl aziridines as N-containing three-atom components in a rhodium-catalyzed [4+3] cycloaddition reaction is described. The reaction proceeds well with various silyl dienol ethers and vinyl aziridines, and enables the efficient synthesis of highly functionalized azepines in an enantioselective manner with net inversion of absolute configuration. The salient features of the transformation include the use of readily available substrates, high selectivity, and mild reaction conditions, as well as the versatile functionalization of the products.
引用
收藏
页码：1351 / 1355
页数：5
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