The tethered aminohydroxylation (TA) of cyclic allylic carbamates.
The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of both regio- and stereoselectivity: the formation of syn-aminodiol motifs is now straightforward using this chemistry. Proof of the mechanism was obtained with an X-ray crystal structure of an azaglycolate osmate ester intermediate.
Donohoe
Timothy J
TJ
Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, UK. timothy.donohoe@chem.ox.ac.uk
Johnson
Peter D
PD
Cowley
Andrew
A
Keenan
Martine
M