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 Aug. 2018
Accepted
21 Sept. 2018
First published
21 Sept. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements