N-Protected a-amino-a-vinyl-g-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO2Et to novel silylated a-ylidene-g-butyrolactones 2, through ring opening of the intermediate aziridine and loss of the trimethylsilyl group. The stereoselective synthesis of compounds 2, by cross-coupling reactions between a-[(triflyloxy)ylidene]-g-butyrolactones 3 and tris[(trimethylsilyl)methyl]aluminum, is also described.

M., C., Gambacorta, A., Gasperi, T., M. A., L., P. A., T. (2006). α-Amino α-Vinyl-γ-butyrolactone Derivatives from α-(Trimethylsilanylmethyl)ylidene-γ-butyrolactones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 22, 5076-5082 [10.1002/ejoc.200600540].

α-Amino α-Vinyl-γ-butyrolactone Derivatives from α-(Trimethylsilanylmethyl)ylidene-γ-butyrolactones

GAMBACORTA, Augusto;GASPERI, TECLA;
2006-01-01

Abstract

N-Protected a-amino-a-vinyl-g-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO2Et to novel silylated a-ylidene-g-butyrolactones 2, through ring opening of the intermediate aziridine and loss of the trimethylsilyl group. The stereoselective synthesis of compounds 2, by cross-coupling reactions between a-[(triflyloxy)ylidene]-g-butyrolactones 3 and tris[(trimethylsilyl)methyl]aluminum, is also described.
2006
M., C., Gambacorta, A., Gasperi, T., M. A., L., P. A., T. (2006). α-Amino α-Vinyl-γ-butyrolactone Derivatives from α-(Trimethylsilanylmethyl)ylidene-γ-butyrolactones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 22, 5076-5082 [10.1002/ejoc.200600540].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11590/117466
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