Organocatalytic Asymmetric α-C-H Allylation of N-Arylidene-Protected Alkyl Amines

Chiral amines represent significant synthetic targets in organic chemistry, as their synthesis holds significant value in drug innovation. Despite asymmetric α-functionalization of amines having been well developed as a powerful strategy, α-C-H functionalization of alkyl amines remains less explored due to the inert nature of such C-H bonds. Herein, we report an asymmetric α-C-H allylation of N-arylidene-protected alkyl amines with MBH carbonates, catalyzed by cost-effective, commercially available hydroquinidine. This method affords diverse chiral γ-amino acid esters in high yields (up to 97%), excellent diastereoselectivities (up to >20:1 dr), and enantioselectivities (up to 99% ee). The reaction features a broad substrate scope, scalability, and facile transformation of products into biologically relevant γ-lactams.