Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides

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• 作者：Dr. Sukalyan Bhadra and Prof. Dr. Hisashi Yamamoto
• 刊名：Angewandte Chemie International Edition
• 出版年：2016
• 出版时间：October 10, 2016
• 年：2016
• 卷：55
• 期：42
• 页码：13043-13046
• 全文大小：765K
• ISSN：1521-3773

文摘

Direct asymmetric synthesis of N-chiral amine oxides was accomplished (up to 91:9 e.r.) by means of a bimetallic titanium catalyst. A hydroxy group situated at the γ-position of the N stereocenter enables the desired N-oxidation through dynamic kinetic resolution of the trivalent amine substrates. The method was further extended to the kinetic resolution of racemic γ-amino alcohols with a preexisting stereocenter, giving an important class of enantioenriched (up to 99.9:0.1 e.r.) building blocks that are otherwise difficult to synthesize.