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Alkene syn dihydroxylation with malonoyl peroxides

Griffith, James C., Jones, Kevin Mark, Picon, Sylvain, Rawling, Michael J., Kariuki, Benson, 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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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 Feb 2020 21:21

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