Stereoselective 1,4-addition of Grignard reagents to chiral γ-alkoxy-α,β-unsaturated ketones

Article abstract of DOI:10.1016/S0957-4166(97)00520-X

Copper-catalyzed conjugate addition reactions of Grignard reagents to γ-alkoxy-α,β-unsaturated ketones, derived from mandelic acid, have been studied. Diastereoselectivity is strongly dependent on the nature of the γ-alkoxy protection group. Bulky silyl protection gives poor stereoselectivities, whereas the ketone bearing benzyloxymethylene (BOM) protection reacts with excellent yields and stereoselectivities.