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Título : Asymmetric Mannich-Type Addition of Ketene Silyl Acetals and Thioacetals to N,N-Dialkylhydrazones
Autor : Díez, Elena, Prieto, Auxiliadora, Simon, Monika, Vázquez, Juan, Álvarez, Eleuterio, Fernández, Rosario, Lassaletta, José M.
Palabras clave : Asymmetric synthesis
Hydrazones
Ketene silyl acetals
Ketene silyl thioacetals
Diastereoselectivity
Fecha de publicación : 11-Jan-2006
Editor: Thieme
Citación : Synthesis - Journal of Synthetic Organic Chemistry (3): 540-550 (2006)
Resumen: The choice of the 2,6-diphenylpiperidine moiety as the N,N-dialkylamino auxiliary in simple aliphatic dialkylhydrazones and the use of scandium triflate as the catalyst in aqueous media appear as the key strategies that enable the highly diastereoselective nucleophilic addition of ketene silyl acetals and thioacetals. The reaction proceeds to afford the expected adducts in high yields (88-98%) and diastereomeric ratios of up to 99:1. N-N bond cleavage of adducts affords enantiomerically pure β-amino esters.
Descripción : 11 páginas, 2 figuras, 2 tablas, 5 esquemas.
Versión del editor: http://dx.doi.org/10.1055/s-2006-926283
URI : http://hdl.handle.net/10261/37863
ISSN: 0039-7881
DOI: 10.1055/s-2006-926283
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