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...

Ausführliche Beschreibung

Bibliographische Detailangaben
Hauptverfasser: Donohoe, T, Blades, K, Moore, P, Waring, M, Winter, J, Helliwell, M, Newcombe, N, Stemp, G
Format: Journal article
Sprache:English
Veröffentlicht: 2002
Beschreibung
Zusammenfassung: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.