Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 14, Pages 4978-4983Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja710922h
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- NIGMS NIH HHS [R01 GM064451, R01 GM064451-07, GM-64451] Funding Source: Medline
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The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allyIB(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 (1), 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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