Indium-promoted chemo- and diastereoselective allylation of α,β-epoxy ketones with potassium allyltrifluoroborate.
A practical method for the chemo- and diastereoselective allylation of α,β-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,β-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6.
Farhad
F
Nowrouzi
John
J
Janetzko
Robert A
RA
Batey