Directed Dihydroxylation of Cyclic Allylic Alcohols and Trichloroacetamides Using OsO4/TMEDA
The Journal of Organic Chemistry2002Vol. 67(23), pp. 7946–7956
Citations Over TimeTop 10% of 2002 papers
Timothy J. Donohoe, Kevin Blades, Peter R. Moore, Michael J. Waring, Jon Winter, Madeleine Helliwell, Nicholas J. Newcombe, Geoffrey Stemp
Abstract
The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.
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