Enantioselective C-H Annulation of Indoles with Diazo Compounds through a Chiral Rh(III) Catalyst

被引:81
作者
Chen, Xiaohong [1 ]
Yang, Shujing [1 ]
Li, Helong [1 ]
Wang, Bo [1 ]
Song, Guoyong [1 ]
机构
[1] Beijing Forestry Univ, Beijing Key Lab Lignocellulos Chem, Beijing 100083, Peoples R China
关键词
enantioselective; C-H annulation; rhodium; indole; diazo ester; FRIEDEL-CRAFTS ALKYLATION; CYCLOPENTADIENYL LIGANDS; BIARYL COMPOUNDS; BOND ADDITION; N BOND; FUNCTIONALIZATION; ACTIVATION; ALKENES; ALKYNES; COMPLEXES;
D O I
10.1021/acscatal.7b00104
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The asymmetric C-H annulation of O-pivaloyl 1-indolehydroxamic acid with donor/acceptor diazo compounds has been achieved for the first time, to the best of our knowledge, by using a rhodium catalyst embedded in a chiral binaphthyl backbone. This protocol constitutes a straightforward route for the synthesis of a new family of 1,2-dihydro-3H-imidazo[1,5-a]indol-3-one derivatives having a quaternary carbon stereocenter in high yields and excellent enantioselectivity (up to 98:2 er).
引用
收藏
页码:2392 / 2396
页数:5
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