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

Catalytic functionality of new optically active thiourea fused gamma-amino alcohols was examined in the asymmetric Mannich reaction of beta-keto active methylene compounds with imines to afford chiral Mannich products, beta-amino keto compounds, with continuous chiral centers, that are versatile synthetic intermediates for deriving various biologically active compounds. In particular, the thiourea fused gamma-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).

Automated summary

The catalytic functionality of new optically active thiourea fused gamma-amino alcohols was investigated in the asymmetric Mannich reaction. Chiral Mannich products, beta-amino keto compounds, with continuous chiral centers were obtained in excellent chemical yield (up to 88%) and stereoselectivities (up to syn : anti/93 : 7 dr, up to 99% ee), making them versatile synthetic intermediates for deriving various biologically active compounds.