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Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis
Author(s) -
Zhao Xiaohu,
Xu Haiyan,
Huang Xiaolei,
Zhou Jianrong Steve
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809930
Subject(s) - reductive amination , chemistry , nickel , formic acid , catalysis , amination , organic chemistry , enantioselective synthesis , nucleophile , alkoxide , reductive elimination , reagent , combinatorial chemistry
Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high‐pressure hydrogen gas.
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