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Nickel‐Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide
Author(s) -
Yang Peng,
Lim Li Hui,
Chuanprasit Pratanphorn,
Hirao Hajime,
Zhou Jianrong Steve
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606821
Subject(s) - reductive amination , chemistry , formic acid , enantioselective synthesis , catalysis , nickel , amination , decarboxylation , formate , hydride , combinatorial chemistry , organic chemistry , stereoselectivity , hydrogen
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 α‐ketoaldehydes and 1,2‐diaminobenzene. Formic acid was used as a safe and economic surrogate for high‐pressure hydrogen gas. Strongly σ‐donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.