Asymmetric Synthesis of β‑Amino Amides by Catalytic Enantioconvergent 2‑Aza-Cope Rearrangement

Dynamic kinetic resolutions of α-stereogenic-β-formyl
amides in asymmetric 2-aza-Cope rearrangements are described. Chiral
phosphoric acids catalyze this rare example of a non-hydrogenative
DKR of a β-oxo acid derivative. The [3,3]-rearrangement occurs
with high diastereo- and enantiocontrol, forming β-imino amides
that can be deprotected to the primary β-amino amide or reduced
to the corresponding diamine.