Alkene syn dihydroxylation with malonoyl peroxides

James C. Griffith; Kevin M. Jones; Sylvain Picon; Michael J. Rawling; Benson M. Kariuki; Matthew Campbell; Nicholas C.O. Tomkinson

doi:10.1021/ja1066674

Alkene syn dihydroxylation with malonoyl peroxides

James C. Griffith, Kevin M. Jones, Sylvain Picon, Michael J. Rawling, Benson M. Kariuki, Matthew Campbell, Nicholas C.O. Tomkinson

Research output: Contribution to journal › Article (Academic Journal) › peer-review

106 Citations (Scopus)

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.

Original language	English
Pages (from-to)	14409-14411
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	41
DOIs	https://doi.org/10.1021/ja1066674
Publication status	Published - 20 Oct 2010

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@article{b55978f25e084cf88e9e728098182151,

title = "Alkene syn dihydroxylation with malonoyl peroxides",

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.",

author = "Griffith, {James C.} and Jones, {Kevin M.} and Sylvain Picon and Rawling, {Michael J.} and Kariuki, {Benson M.} and Matthew Campbell and Tomkinson, {Nicholas C.O.}",

year = "2010",

month = oct,

day = "20",

doi = "10.1021/ja1066674",

language = "English",

volume = "132",

pages = "14409--14411",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Alkene syn dihydroxylation with malonoyl peroxides

AU - Griffith, James C.

AU - Jones, Kevin M.

AU - Picon, Sylvain

AU - Rawling, Michael J.

AU - Kariuki, Benson M.

AU - Campbell, Matthew

AU - Tomkinson, Nicholas C.O.

PY - 2010/10/20

Y1 - 2010/10/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=77958038930&partnerID=8YFLogxK

U2 - 10.1021/ja1066674

DO - 10.1021/ja1066674

M3 - Article (Academic Journal)

C2 - 20866057

AN - SCOPUS:77958038930

SN - 0002-7863

VL - 132

SP - 14409

EP - 14411

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 41

ER -

Alkene syn dihydroxylation with malonoyl peroxides

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