Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (−)-Trigonoliimine A

by Thomas Buyck, Qian Wang, Jieping Zhu*

Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into α,α′-disubstituted α-amino acids. The enantioselective total synthesis of both (+)- and (−)-trigonoliimine A was accomplished using one of the Michael adducts derived from this methodology. M.S.=molecular sieves.

Angewandte Chemie International Edition

DOI: 10.1002/anie.201306663