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

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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

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Publication details

The article was received on 31 Aug 2018, accepted on 21 Sep 2018 and first published on 21 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02141D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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., 2018, Advance Article , DOI: 10.1039/C8OB02141D

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