Bismuth(III) Oxychloride Procatalyst Based One-Pot Multicomponent Synthesis of β′-Acetamido-β-dicarbonyl Compounds with Special Reference to pref-β′-Acetamido-β-oxo Esters

Abstract

Bismuth(III) chloride generated in situ from the procatalyst bismuth(III) oxychloride and acetyl chloride efficiently catalyzes the one-pot synthesis of β′-acetamido-β-dicarbonyl compounds from aldehydes, enolizable β-diketones, or β-oxo esters and acetyl chloride in acetonitrile solution and under solvent-free conditions at room temperature; in the case of the β-oxo ester derived products, these are obtained with moderate to excellent dia­stereoselectivity in favor of the pref-isomer. X-ray crystallographic analysis of one pref-β′-acetamido-β-oxo ester exhibits C-H···O and N-H···O intermolecular interactions in the three-dimensional supramolecular assembly.

Key words

multicomponent reaction - bismuth(III) oxychloride - bismuth(III) chloride - catalysis - β′-acetamido-β-dicarbonyl compounds - diastereoselectivity

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Crystallographic data of the compound pref-16 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 601470. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].