A Powerful Cinchona Alkaloid Derivative for the Henry Reaction

Significance

A cinchona alkaloid derivative (1) catalyzed Henry reaction of nitromethane with various trifluoromethyl ketones is reported. Careful design of the catalyst structure resulted in an exquisite reactivity, providing the products in high yields and enantioselectivities. While the thiourea substituent of the catalyst backbone seems to ­activate the electrophile, the role of the carbamoyl moiety remains unclear. Presumably this subunit controls the conformation of the catalyst during the reaction pathway.