N-Protected a-amino-a-vinyl-gamma-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO(2)Et to novel silylated a-ylidene-gamma-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]-gamma-butyrolactones 3 and tris[(trimethylsilyl)methyl]aluminum, is also described.

Capuzzi, M., Gambacorta, A., Gasperi, T., LORETO M., A., Tardella, P.A. (2006). alpha-Amino-gamma-vinyl-gamma-butyrolactone Derivatives from alpha-{[(Trimethylsilyl)-methyl]alkylidene}-gamma-butyrolactones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 5076-5082 [10.1002/ejoc.200600540].

alpha-Amino-gamma-vinyl-gamma-butyrolactone Derivatives from alpha-{[(Trimethylsilyl)-methyl]alkylidene}-gamma-butyrolactones

GASPERI, TECLA;
2006-01-01

Abstract

N-Protected a-amino-a-vinyl-gamma-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO(2)Et to novel silylated a-ylidene-gamma-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]-gamma-butyrolactones 3 and tris[(trimethylsilyl)methyl]aluminum, is also described.
Capuzzi, M., Gambacorta, A., Gasperi, T., LORETO M., A., Tardella, P.A. (2006). alpha-Amino-gamma-vinyl-gamma-butyrolactone Derivatives from alpha-{[(Trimethylsilyl)-methyl]alkylidene}-gamma-butyrolactones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 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/11590/146868
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