Alkene syn dihydroxylation with malonoyl peroxides.
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.
Griffith
James C
JC
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, UK.
Jones
Kevin M
KM
Picon
Sylvain
S
Rawling
Michael J
MJ
Kariuki
Benson M
BM
Campbell
Matthew
M
Tomkinson
Nicholas C O
NC
D000475:Alkenes / Q000737:chemistry*; D006900:Hydroxylation; D010545:Peroxides / Q000737:chemistry*
D000475:Alkenes; D010545:Peroxides