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Closed Access item Asymmetric Mannich-Type Addition of Ketene Silyl Acetals and Thioacetals to N,N-Dialkylhydrazones

Authors:Díez, Elena
Prieto, Auxiliadora
Simon, Monika
Vázquez, Juan
Álvarez, Eleuterio
Fernández, Rosario
Lassaletta, José M.
Keywords:Asymmetric synthesis, Hydrazones, Ketene silyl acetals, Ketene silyl thioacetals, Diastereoselectivity
Issue Date:11-Jan-2006
Citation:Synthesis - Journal of Synthetic Organic Chemistry (3): 540-550 (2006)
Abstract: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.
Description:11 páginas, 2 figuras, 2 tablas, 5 esquemas.
Publisher version (URL):http://dx.doi.org/10.1055/s-2006-926283
E-ISSNmetadata.dc.identifier.doi = DOI:1437-210X
Appears in Collections:(IIQ) Artículos

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