Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds

by Sylvie Goncalves-Contal, Ludovic Gremaud, Alexandre Alexakis*

Picture perfect: By using the reagent trimethylaluminium and β,γ-unsaturated α-ketoamides, 1,4-adducts were obtained with perfect 1,4-regioselectivity and good to excellent yields and ee values. The potential synthetic utility of the methodology was highlighted by preparation of γ-methyl-substituted carbonyls, key synthons to many natural products. binap=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, TC=thiophene carboxylate.

Angewandte Chemie International Edition

DOI: 10.1002/anie.201306541