A Designed Amide as an Aldol Donor in the Direct Catalytic Asymmetric Aldol Reaction

The direct catalytic asymmetric aldol reaction offers efficient access to beta-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of alpha-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic beta-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Bronsted base.