Details

Autor(en) / Beteiligte

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

Titel

Alkene Syn Dihydroxylation with Malonoyl Peroxides

Ist Teil von

• Journal of the American Chemical Society, 2010-10, Vol.132 (41), p.14409-14411

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2010

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.