Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.
An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH]2 and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to >20:1.
Menard
Frederic
F
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.
Chapman
Timothy M
TM
Dockendorff
Chris
C
Lautens
Mark
M
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D012238:Rhodium / Q000737:chemistry*
D001897:Boronic Acids; D012238:Rhodium