Catalytic Hydrogenation of α,β-Epoxy Ketones to Form β-Hydroxy Ketones Mediated by an NADH Coenzyme Model

Hua-Jian Xu,† You-Cheng Liu,*†‡ Yao Fu,† and Yun-Dong Wu*§;
Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, College of Chemistry, Lanzhou University, Lanzhou, 730000, China, Department of Chemistry, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China, and College of Chemistry, Peking University, Beijing, China
Org. Lett., 2006, 8 (16), pp 3449–3451
DOI: 10.1021/ol0610892
Publication Date (Web): July 7, 2006
Copyright © 2006 American Chemical Society
†

 University of Science and Technology of China.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Lanzhou University.

,
§

 Hong Kong University of Science and Technology.

,

 Peking University.

, ycliu@ustc.edu.cn, ; , chydwu@ust.hk

Abstract

Abstract Image

The hydrogenation of α,β-epoxy ketones can be mediated by a catalytic amount of BNAH or BNA+Br- to form corresponding β-hydroxy ketones in high yield. Na2S2O4 is used as the reducing agent to convert BNA+Br- to BNAH. A radical mechanism has been proposed to understand many observations of this catalytic reaction.

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History

  • Published In Issue August 03, 2006
  • Received May 4, 2006

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