- Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.
Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles.
Organic letters (2006-09-22)
Frederic Menard, Timothy M Chapman, Chris Dockendorff, Mark Lautens
PMID16986952
ABSTRACT
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.
MATERIALS