Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide

被引：101

作者：

Yang, Peng ^{[1
]}

Lim, Li Hui ^{[1
]}

Chuanprasit, Pratanphorn ^{[1
]}

Hirao, Hajime ^{[1
]}

Zhou, Jianrong ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 39期

关键词：

chiral alkylamines; nickel; reductive amination; synthetic methods; transfer hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; N-ARYL IMINES; DYNAMIC KINETIC RESOLUTION; AMINO-ACID DERIVATIVES; BRONSTED ACID; COOPERATIVE CATALYSIS; PRACTICAL SYNTHESIS; PHOSPHORUS LIGANDS; ACYCLIC IMINES; COMPLEXES;

D O I：

10.1002/anie.201606821

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one-pot synthesis of tetrahydroquinoxalines was also developed starting directly from alpha-ketoaldehydes and 1,2-diaminobenzene. Formic acid was used as a safe and economic surrogate for high-pressure hydrogen gas. Strongly sigma-donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.

引用

页码：12083 / 12087

页数：5

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