American Chemical Society
ol200923p_si_002.cif (38.28 kB)

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

Download (38.28 kB)
posted on 2011-06-17, 00:00 authored by Vanesa Marcos, Jose Alemán, Jose L. Garcia Ruano, Francesca Marini, Marcello Tiecco
A new organocatalytic approach for the synthesis of a variety of α-alkyl, α-phenylselenyl ketones as well as their corresponding esters and amides, by the addition of α-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 %.