Issue 16, 2019

Secondary amines as coupling partners in direct catalytic asymmetric reductive amination

Abstract

The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of a selected additive set under mild conditions (0–25 °C). The applied chiral phosphoramidite ligands are readily prepared from BINOL and easily modified. Compared with common tertiary chiral amine synthetic methods, this procedure is much more concise and scalable, as exemplified by the facile synthesis of rivastigmine and N-methyl-1-phenylethanamine.

Graphical abstract: Secondary amines as coupling partners in direct catalytic asymmetric reductive amination

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Jan 2019
Accepted
12 Mar 2019
First published
14 Mar 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 4509-4514

Secondary amines as coupling partners in direct catalytic asymmetric reductive amination

Z. Wu, S. Du, G. Gao, W. Yang, X. Yang, H. Huang and M. Chang, Chem. Sci., 2019, 10, 4509 DOI: 10.1039/C9SC00323A

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