Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural a-angelica lactone has been successfully developed. It was demonstrated that the nonactivated natural a-angelica lactone Is a useful vinylogous nucleophile to give the chiral delta-amino gamma,gamma-disubstituted butenolide carbonyl derivatives. The N,N'-dioxide L2-Se-III complex is efficient toward tie obtention of a range of corresponding products with adjacent quaternary and tertiary stereocenters in excellent dr and ee values.