Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines

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• 作者：Sayantani Das ; Nilanjana Majumdar ; Chandra Kanta De ; Dipti Sankar Kundu ; Arno Döhring ; Anika Garczynski ; Benjamin List
• 刊名：Journal of the American Chemical Society
• 出版年：2017
• 出版时间：February 1, 2017
• 年：2017
• 卷：139
• 期：4
• 页码：1357-1359
• 全文大小：331K
• ISSN：1520-5126

文摘

A Brønsted acid catalyzed kinetic resolution of primary amines is described that is based on the condensation between an amine and a carbonyl compound. 1,3-Diketones react with racemic α-branched amines to furnish the corresponding enantioenriched enaminone and recovered starting material. Good to excellent enantioselectivity was observed with both aromatic and aliphatic primary amines. This process represents the first small-molecule catalyzed kinetic resolution of aliphatic amines.