Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA.

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 pres...

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Detalles Bibliográficos
Autores principales: Donohoe, T, Blades, K, Moore, P, Waring, M, Winter, J, Helliwell, M, Newcombe, N, Stemp, G
Formato: Journal article
Lenguaje:English
Publicado: 2002
Descripción
Sumario: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.