Asymmetric Ni-Catalyzed Conjugate Allylation of Activated Enones
Journal of the American Chemical Society2008Vol. 130(14), pp. 4978–4983
Citations Over TimeTop 10% of 2008 papers
Abstract
The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The reaction appears to proceed by conversion of the dialkylidene ketone substrate to an unsaturated pi-allyl complex (I), followed by reductive elimination. Enantioselectivities range from 91 to 94% ee for a range of substrates when chiral ligand 14 is employed.
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