1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones

1,3-Diamine-derivedcatalysts were designed, synthesized, and usedin asymmetric Mannich reactions of ketones. The reactions catalyzedby one of the 1,3-diamine derivatives in the presence of acids affordedthe Mannich products with high enantioselectivities under mild conditions.In most cases, bond formation occurred at the less-substituted & alpha;-positionof the ketone carbonyl group. Our results indicate that the primaryand the tertiary amines of the 1,3-diamine derivative cooperativelyact for the catalysis.

Automated summary

1,3-Diamine-derived catalysts were synthesized and utilized in asymmetric Mannich reactions of ketones. The Mannich products with high enantioselectivities were obtained under mild conditions through catalysis by one of the 1,3-diamine derivatives in the presence of acids. Bond formation primarily occurred at the less-substituted α-position of the ketone carbonyl group. The primary and tertiary amines of the 1,3-diamine derivative cooperatively acted for the catalysis.