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. BiaggiPrimo
;M. Benaglia
;A. PuglisiUltimo
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.File | Dimensione | Formato | |
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