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镍催化下磺酰胺、氨基磺酸酯和磷酰胺的不对称逐步还原胺化反应。

Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis.

作者信息

Zhao Xiaohu, Xu Haiyan, Huang Xiaolei, Zhou Jianrong Steve

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, SPMS-CBC-06-06, Singapore, 637371, Singapore.

出版信息

Angew Chem Int Ed Engl. 2019 Jan 2;58(1):292-296. doi: 10.1002/anie.201809930. Epub 2018 Dec 5.

DOI:10.1002/anie.201809930
PMID:30375715
Abstract

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.

摘要

在镍催化剂和钛醇盐存在下实现了亲核性较差的磺酰胺的不对称还原胺化反应。包括可烯醇化酮和一些联芳基酮在内的多种酮,都能以优异的对映体过量转化为磺酰胺。氨基磺酸酯的环化反应以及二芳基膦酰胺的分子间还原胺化反应也取得了成功。甲酸被用作高压氢气的安全且经济的替代物。

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