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

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

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 e...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 139; no. 4; pp. 1357 - 1359
Main Authors: Das, Sayantani, Majumdar, Nilanjana, De, Chandra Kanta, Kundu, Dipti Sankar, Döhring, Arno, Garczynski, Anika, List, Benjamin
Format: Journal Article
Language:English
Published: United States American Chemical Society 01-02-2017
Online Access:Get full text
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Summary: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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b12176