Highly Regioselective, Catalytic Asymmetric Reductive Coupling of 1,3-Enynes and Ketones

Organic Letters 7(14), 3077-3080, DOI: 10.1021/ol051075g

Highly regioselective, catalytic asymmetric reductive coupling reactions of 1,3-enynes and ketones have been achieved using catalytic amounts of Ni(cod)2 and a P-chiral, monodentate ferrocenyl phosphine ligand. These couplings represent the first examples of catalytic, intermolecular reductive coupling of alkynes and ketones, enantioselective or otherwise, and afford synthetically useful 1,3-dienes possessing a quaternary carbinol stereogenic center in up to 70% ee.