Enantioselective Rh-Catalyzed Carboacylation of C=N Bonds via C-C Activation of Benzocyclobutenones

被引：113

作者：

Deng, Lin ^{[1
]}

Xu, Tao ^{[1
,2
]}

Lo, Hongbo

Done, Guangbin ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

[2] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Qingdao 266003, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 01期

关键词：

CROSS-COUPLING REACTIONS; OLEFIN INSERTION; RHODIUM; CLEAVAGE; CHEMISTRY; FUNCTIONALIZATION; CYCLOBUTENONES; COMPLEXES; ALKALOIDS; REAGENTS;

D O I：

10.1021/jacs.5b11120

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we describe the first enantioselective Rh catalyzed carboacylation of mimes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C=N bond, which provides a unique approach to access chiral lactams. A range of polycydic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.

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页码：369 / 374

页数：6

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