An Asymmetric Route to β-Aminoalanine Derivatives through Michael Addition of Amides, Imides, and Isatins to a Chiral Dehydroalanine Ni(II) Complex

The asymmetric synthesis of β-aminoalanine derivatives containing an amide, imide, and isatin fragment through the Michael addition reaction is presented. The coupling of a chiral dehydroalanine Ni(II) complex with amides, imides, and isatins catalyzed by base afforded modified Ni(II) complexes with high diastereoselectivity. Decomposition of the selected complex with HCl gave an α-amino acid with a morpholinone fragment as well as its α-deuterated analogue. Functionalization of an isatin-containing Ni(II) complex through a 1,3-cycloaddition reaction and subsequent acid-induced decomposition led to a spiro diamino diacid.