Alkene syn dihydroxylation with malonoyl peroxides

Griffith, James C., Jones, Kevin Mark, Picon, Sylvain, Rawling, Michael J., Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Campbell, Matthew and Tomkinson, Nicholas Charles Oliver 2010. Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society 132 (41) , pp. 14409-14411. 10.1021/ja1066674

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Abstract

Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40−93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0002-7863
Last Modified:	05 Dec 2022 10:04
URI:	https://orca.cardiff.ac.uk/id/eprint/20138

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