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 presented and a plausible mechanism described.
Donohoe
Timothy J
TJ
Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, UK. timothy.donohoe@chem.ox.ac.uk
Blades
Kevin
K
Moore
Peter R
PR
Waring
Michael J
MJ
Winter
Jon J G
JJ
Helliwell
Madeleine
M
Newcombe
Nicholas J
NJ
Stemp
Geoffrey
G