Issue 7, 2019

Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols

Abstract

In this protocol we described a boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles. This diastereo- and enantiospecific reaction provides an efficient entry to prepare a variety of hydroxyl sulfides. Through the directing effect of the hydroxyl group, nucleophilic attack on the C-3 position of the epoxide moiety is favoured. It can be rationalized in a proposed transition state, in which the boronic acid catalyst tethers both epoxides and S-nucleophiles.

Graphical abstract: Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols

Supplementary files

Article information

Article type
Paper
Submitted
31 ago. 2018
Accepted
21 sep. 2018
First published
21 sep. 2018

Org. Biomol. Chem., 2019,17, 1901-1905

Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols

H. Yao, J. Liu and C. Wang, Org. Biomol. Chem., 2019, 17, 1901 DOI: 10.1039/C8OB02141D

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