Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Direct enolate formation
coupled with subsequent enantioselective
C–C bond formation remains a topic of intense interest in asymmetric
catalysis. This methodology is achieved even with low acidic amides
without an electron-withdrawing group at the α-position in the
context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type
7-azaindoline amides served as enolate precursors to afford the desired
Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency
provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures
the synthetic utility of the Mannich adducts.