10.1021/ja710922h.s002
Joshua D. Sieber
Joshua D.
Sieber
James P. Morken
James P.
Morken
Asymmetric Ni-Catalyzed Conjugate Allylation of Activated
Enones
American Chemical Society
2008
benzylidene site
dialkylidene ketones
dialkylidene ketone substrate
reductive elimination
nonsymmetric substrates
chiral ligand 14
allylboronic acid pinacol ester
Enantioselectivities range
2008-04-09 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Asymmetric_Ni_Catalyzed_Conjugate_Allylation_of_Activated_Enones/2945758
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 π-allyl complex (<b>I</b>), followed by reductive elimination.
Enantioselectivities range from 91 to 94% ee for a range of substrates when chiral ligand <b>14</b> is
employed.