Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of ß-keto active methylene compounds with imines.

ABSTRACT

Catalytic functionality of new optically active thiourea fused γ-amino alcohols was examined in the asymmetric Mannich reaction of ß-keto active methylene compounds with imines to afford chiral Mannich products, ß-amino keto compounds, with continuous chiral centers, that are versatile synthetic intermediates for deriving various biologically active compounds. In particular, the thiourea fused γ-amino alcohols showed satisfactory catalytic activity in this reaction and afforded chiral Mannich products in excellent chemical yield (up to 88%) and stereoselectivities (up to syn anti/93 7 dr, up to 99% ee).