Asymmetric Synthesis of alpha-Alkyl alpha-Selenocarbonyl Compounds Catalyzed by Bifunctional Organocatalysts

A new organocatalytic approach for the synthesis of a variety of alpha-alkyl, alpha-phenylselenyl ketones as well as their corresponding esters and amides, by the addition of alpha-selenocarbonyl derivatives to nitroalkenes catalyzed by thiourea or squaramide cinchona catalysts, is presented. This catalytic system allows the preparation in high yields of enantiomerically enriched selenocarbonyl derivatives bearing two chiral centers with excellent ee's and dr's by using catalytic loadings of 3 mol %.