Highly regio- and diastereoselective halohydroxylation of olefins: a facile synthesis of vicinal halohydrins

被引：31
|
作者：
Zhang, Jinglei [1 ]
Wang, Jie [1 ]
Qiu, Zhuibai [1 ]
Wang, Yang [1 ,2 ]
机构：
[1] Fudan Univ, Sch Pharm, Dept Med Chem, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 36期
基金：
中国国家自然科学基金;
关键词：
Chlorohydroxylation; Chlorohydrin; Bromohydroxylation; Bromohydrin; Olefin; REGIOSELECTIVE CONVERSION; N-HALOSUCCINIMIDES; BETA-CYCLODEXTRIN; VIC-HALOHYDRINS; METAL-HALIDES; IN-SITU; EPOXIDES; BROMIDE; BROMINATION; ALKENES;
D O I：
10.1016/j.tet.2011.06.077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-L-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6859 / 6867
页数：9
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