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Ethyl Glyoxylate N-Tosylhydrazone as Sulfonyl-Transfer Reagent in Base-Catalyzed Sulfa-Michael Reactions

Maitane Fernández, Uxue Uria, Lucia Orbe, Jose L. Vicario*, Efraím Reyes and Luisa Carrillo

*Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P.O. Box 644, E-48080 Bilbao, Spain, Email: joseluis.vicarioehu.es

M. Fernández, U. Uria, L. Orbe, J. L. Vicario, E. Reyes, L. Carrillo, J. Org. Chem., 2014, 79, 230-239.

DOI: 10.1021/jo402518q (free Supporting Information)


Abstract

Ethyl glyoxylate N-tosylhydrazone is an excellent sulfonyl anion surrogate in a DBU-catalyzed conjugate addition reaction with enones and enals for the synthesis of functionalized sulfones. The reaction provides γ-keto- and γ-hydroxy sulfones in a simple and reliable way through a sulfa-Michael reaction that proceeds with good yield and chemoselectivity.

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Key Words

sulfones, Michael addition


ID: J42-Y2014