Thiazolium-catalyzed additions of acylsilanes: a general strategy for acyl anion addition reactions

AE Mattson, AR Bharadwaj, AM Zuhl…

Index: Mattson, Anita E.; Bharadwaj, Ashwin R.; Zuhl, Andrea M.; Scheidt, Karl A. Journal of Organic Chemistry, 2006 , vol. 71, # 15 p. 5715 - 5724

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Citation Number: 118

Abstract

A strategy utilizing N-heterocyclic carbenes (NHCs) derived from thiazolium salts has been developed for the generation of carbonyl anions from acylsilanes. Synthetically useful 1, 4- diketones and N-phosphinoyl-α-aminoketones have been prepared in good to excellent yields via NHC-catalyzed additions of acylsilanes to the corresponding α, β-unsaturated systems and N-phosphinoylimines. These organocatalytic reactions are air-and water- ...