Article ID Journal Published Year Pages File Type
5221832 Tetrahedron 2011 9 Pages PDF
Abstract

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.

Graphical abstractDirect halohydroxylation of olefins provided a facile synthesis of vic-halohydrins in excellent yield with high chemo-, regio- and stereoselectivityDownload full-size image.

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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