Abstract
A new, versatile reagent, N,N,N-triphenylselenyl-isocyanuric acid (TPSCA) has been prepared, characterized, and used
as a source of the electrophilic phenylselenyl group. This relatively stable compound
was utilized for an efficient α-selenenylation reaction of aldehydes and ketones catalyzed
by l-prolinamide under mild reaction conditions. The organocatalytic asymmetric α-selenenylation
of an aldehyde was also studied and the reaction was found to proceed with high enantioselectivity
(96% ee).
Key words
electrophilic selenenylation - isocyanuric acid - aldehydes - ketones - prolinamide