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Title: | Asymmetric Mannich-Type Addition of Ketene Silyl Acetals and Thioacetals to N,N-Dialkylhydrazones |
Authors: | Díez, Elena; Prieto, María Auxiliadora CSIC ORCID ; Simon, Monika; Vázquez, Juan; Álvarez, Eleuterio CSIC ORCID ; Fernández, Rosario; Lassaletta, José M. CSIC ORCID | Keywords: | Asymmetric synthesis Hydrazones Ketene silyl acetals Ketene silyl thioacetals Diastereoselectivity |
Issue Date: | 11-Jan-2006 | Publisher: | Thieme | 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 | URI: | http://hdl.handle.net/10261/37863 | DOI: | 10.1055/s-2006-926283 | ISSN: | 0039-7881 | E-ISSN: | 1437-210X |
Appears in Collections: | (IIQ) Artículos |
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