Synthesis 2014; 46(21): 2910-2916
DOI: 10.1055/s-0034-1378891
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts

Ming-Lei Yuan, Jian-Hua Xie*, Xiao-Hui Yang, Qi-Lin Zhou*
  • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China   Fax: +86(22)23506177   Email: jhxie@nankai.edu.cn   Email: qlzhou@nankai.edu.cn
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Publication History

Received: 17 May 2014

Accepted after revision: 04 July 2014

Publication Date:
06 August 2014 (eFirst)

Abstract

A highly efficient iridium-catalyzed asymmetric hydrogenation of α-amino ketones for the synthesis of chiral 1,2-amino alcohols is described. With chiral spiro iridium catalyst Ir-(R)-1c, a series of α-amino ketones were hydrogenated to chiral β-amino alcohols in excellent enantioselectivities (up to 99.9% ee) with TON up to 100 000. In addition, with this highly efficient method the chiral drugs (R)-clorpenaline and (R)-phenylephrine were prepared in very high efficiency.

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