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Boronic Acid-Catalysed C-3 Selective Ring Opening of 3,4-epoxy Alcohols With Thiophenols and Thiols

Hongqing Yao, Jiawei Liu, Chuan Wang

Org Biomol Chem. 2019 Feb 13;17(7):1901-1905.

PMID: 30259944

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS7931222 (6-hydroxypyridin-3-yl)boronic acid (6-hydroxypyridin-3-yl)boronic acid Price
LS7931253 5-cyano-3-pyridinyl boronic acid 5-cyano-3-pyridinyl boronic acid Price
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