Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile

被引：128

作者：

Gribble, Michael W., Jr. ^{[1
]}

Guo, Sheng ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 15期

基金：

美国国家卫生研究院;

关键词：

ENANTIOSELECTIVE ADDITION; REGIOSELECTIVE 1,4-HYDROBORATION; 1-ACYLPYRIDINIUM SALTS; CONVENIENT METHOD; DEAROMATIZATION; REAGENTS; HYDROSILYLATION; HYDROBORATION; ALKYLATION; ALKYNES;

D O I：

10.1021/jacs.8b02568

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We show that a chiral copper hydride (CuH) complex catalyzes C-C bond-forming dearomatization of pyridines and pyridazines at room temperature. The catalytic reaction operates directly on free hetero-cycles and generates the nucleophiles in situ, eliminating the need for stoichiometric preactivation of either reaction partner; further, it is one of very few methods available for the enantioselective 1,4-dearomatization of heteroarenes. Combining the dearomatization with facile derivatization steps enables one-pot syntheses of enantioenriched pyridines and piperidines.

引用

收藏

页码：5057 / 5060

页数：4

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