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通过动态动力学拆分实现醛的催化不对称还原胺化反应。

Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution.

作者信息

Hoffmann Sebastian, Nicoletti Marcello, List Benjamin

机构信息

Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany.

出版信息

J Am Chem Soc. 2006 Oct 11;128(40):13074-5. doi: 10.1021/ja065404r.

DOI:10.1021/ja065404r
PMID:17017786
Abstract

A novel organocatalytic asymmetric reductive amination of aldehydes has been developed. Treating racemic alpha-branched aldehydes with p-anisidine and a Hantzsch ester in the presence of our previously developed phosphoric acid catalyst, TRIP, gave beta-branched secondary amines in excellent yields and enantioselectivities via an efficient dynamic kinetic resolution. The process is applicable to several different aromatic aldehydes and amines but gives slightly reduced enantiomeric ratios with aliphatic aldehydes.

摘要

一种新型的醛的有机催化不对称还原胺化反应已被开发出来。在我们之前开发的磷酸催化剂TRIP存在下,用对甲氧基苯胺和汉斯酯处理外消旋α-支链醛,通过高效的动态动力学拆分,以优异的产率和对映选择性得到β-支链仲胺。该方法适用于几种不同的芳香醛和胺,但对于脂肪醛,对映体比例略有降低。

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