The stereoselective aldol-type synthesis of optically active β-hydroxy hydrazones and β-hydroxy ketones mediated by chiral α-sulphinyl hydrazones is described. In some cases a good degree of enantioselectivity (up to 88%) is achieved. The factors affecting the stereochemical outcome of the process, i.e. the nature and stoicheiometry of the base and the structures and steric requirements of the α-sulphinyl hydrazones are discussed.
Chiral alpha-sulfinyl hydrazones as effective reagents for stereoselective aldoltype condensation / R. Annunziata, F. Cozzi, M. Cinquini, L. Colombo, C.M.A. Gennari, G. Poli, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 2(1985), pp. 251-254. [10.1039/p19850000251]
Chiral alpha-sulfinyl hydrazones as effective reagents for stereoselective aldoltype condensation
R. Annunziata;F. Cozzi;M. Cinquini;C.M.A. Gennari;C. Scolastico
1985
Abstract
The stereoselective aldol-type synthesis of optically active β-hydroxy hydrazones and β-hydroxy ketones mediated by chiral α-sulphinyl hydrazones is described. In some cases a good degree of enantioselectivity (up to 88%) is achieved. The factors affecting the stereochemical outcome of the process, i.e. the nature and stoicheiometry of the base and the structures and steric requirements of the α-sulphinyl hydrazones are discussed.
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