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

AuthorsDíez, Elena; Prieto, María Auxiliadora ; Simon, Monika; Vázquez, Juan; Álvarez, Eleuterio ; Fernández, Rosario; Lassaletta, José M.
KeywordsAsymmetric synthesis
Ketene silyl acetals
Ketene silyl thioacetals
Issue Date11-Jan-2006
CitationSynthesis - Journal of Synthetic Organic Chemistry (3): 540-550 (2006)
AbstractThe 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.
Description11 páginas, 2 figuras, 2 tablas, 5 esquemas.
Publisher version (URL)http://dx.doi.org/10.1055/s-2006-926283
Appears in Collections:(IIQ) Artículos
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