CC BY ND NC 4.0 · Synlett 2019; 30(04): 437-441
DOI: 10.1055/s-0037-1610385
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Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

Lingsheng Ai
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
,
Weijin Wang
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
,
Jialiang Wei
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
,
Qing Li
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
,
Song Song*
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
b  State Key Laboratory of Drug Research Shanghai Institute of Materia Medical Chinese Academy of Sciences, Shanghai 201203, P. R. of China
,
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   Email: ssong@bjmu.edu.cn   Email: jiaoning@pku.edu.cn
b  State Key Laboratory of Drug Research Shanghai Institute of Materia Medical Chinese Academy of Sciences, Shanghai 201203, P. R. of China
› Author Affiliations
Financial support from the National Basic Research Program of China (973 Program) (grant No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21602005, 21632001, 21772002), and the State Key Laboratory of Drug Research are greatly appreciated.
Further Information

Publication History

Received: 26 August 2018

Accepted after revision: 23 October 2018

Publication Date:
21 November 2018 (eFirst)

 

Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.

Supporting Information

 
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