Synlett 2015; 26(16): 2247-2252
DOI: 10.1055/s-0035-1560051
letter
© Georg Thieme Verlag Stuttgart · New York

N,N,N-Triphenylselenylisocyanuric Acid (TPSCA): A New Versatile Reagent for α-Phenylselenenylation of Aldehydes and Ketones

Barahman Movassagh*
Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran   eMail: bmovass1178@yahoo.com
,
Ahmad Takallou
Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran   eMail: bmovass1178@yahoo.com
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Publikationsverlauf

Received: 22. April 2015

Accepted after revision: 03. Juli 2015

Publikationsdatum:
19. August 2015 (online)


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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).

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