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Secondary Amines as Coupling Partners in Direct Catalytic Asymmetric Reductive Amination

Abstract

The secondary amine participated asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time secondary amines are capable of effectively serving as the N-sources in asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of selected additive set under mild conditions (0~25 oC). 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.

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Publication details

The article was received on 20 Jan 2019, accepted on 12 Mar 2019 and first published on 14 Mar 2019


Article type: Edge Article
DOI: 10.1039/C9SC00323A
Citation: Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    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, Accepted Manuscript , DOI: 10.1039/C9SC00323A

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