Catalytic Intramolecular Ketone Alkylation with Olefins by Dual Activation.
Two complementary methods for catalytic intramolecular ketone alkylation reactions with unactivated olefins, resulting in Conia-ene-type reactions, are reported. The transformations are enabled by dual activation of both the ketone and the olefin and are atom-economical as stoichiometric oxidants or reductants are not required. Assisted by Kool's aniline catalyst, the reaction conditions can be both pH- and redox-neutral. A broad range of functional groups are thus tolerated. Whereas the rhodium catalysts are effective for the formation of five-membered rings, a ruthenium-based system that affords the six-membered ring products was also developed.
Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX 78712 (USA) http://gbdong.cm.utexas.edu/
Hee Nam
HN
Lim
Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX 78712 (USA) http://gbdong.cm.utexas.edu/. gbdong@cm.utexas.edu.
Guangbin
G
Dong
Conia-ene reactions; bicycles; dual catalysis; ketone alkylation; rhodium catalysis