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
收藏
页码：12083 / 12087
页数：5
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