Aminative Umpolung of Aldehydes to α-Amino Anion Equivalents for Pd-Catalyzed Allylation: An Efficient Synthesis of Homoallylic Amines

An attractive strategy for generation of alpha-amino anions from aldehydes with applications in synthesis of homoallylic amines is described. Aromatic aldehydes can be converted to alpha-amino anion equivalents via amination with 2,2-diphenylglycine and Subsequent decarboxylation. The in situ generated alpha-imino anions are highly reactive for Pd-catalyzed allylation, forming the corresponding homoallylic amines in high yields with excellent regioselectivity.