The scandium (III) catalysed condensation of silylketene thioacetals and pyridylthioacetals with imines in pure water was studied. The reaction of the phenylthioacetal derivatives brings always to b-aminoesters; the reaction of pyridylthioacetals leads to the stereoselective formation of b-lactams in organic solvents, while in the presence of a large amount of water affords b-amino amides in good yields. That represents a new, easy, one-pot catalytic synthesis in water of an interesting class of compounds, direct precursors of 1,3-diamino hydroxy compounds. The possibility of recovering and recycling the catalytic systems was also briefly investigated.

Catalysis in water: synthesis of beta-amno amides by Sc(III) promoted condensation of silylketene pyridylthioacetal and imines / C. Biaggi, M. Benaglia, A. Puglisi. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 692:26(2007), pp. 5795-5798.

Catalysis in water: synthesis of beta-amno amides by Sc(III) promoted condensation of silylketene pyridylthioacetal and imines

C. Biaggi
Primo
;
M. Benaglia
;
A. Puglisi
Ultimo
2007

Abstract

The scandium (III) catalysed condensation of silylketene thioacetals and pyridylthioacetals with imines in pure water was studied. The reaction of the phenylthioacetal derivatives brings always to b-aminoesters; the reaction of pyridylthioacetals leads to the stereoselective formation of b-lactams in organic solvents, while in the presence of a large amount of water affords b-amino amides in good yields. That represents a new, easy, one-pot catalytic synthesis in water of an interesting class of compounds, direct precursors of 1,3-diamino hydroxy compounds. The possibility of recovering and recycling the catalytic systems was also briefly investigated.
scandium triflate; catalysis; reaction in water; synthetic method
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/42243
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