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. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
alpha-amino-alpha-vinyl-gamma-butyrolactone derivatives from alpha-{[(trimethylsilyl)-methyl]alkylidene}-gamma-butyrolactones / M., Capuzzi; T., Gasperi; A., Gambacorta; Loreto, Maria Antonietta; Tardella, Paolo Antonio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - issue 22(2006), pp. 5076-5082. [10.1002/ejoc.200600540]
alpha-amino-alpha-vinyl-gamma-butyrolactone derivatives from alpha-{[(trimethylsilyl)-methyl]alkylidene}-gamma-butyrolactones
LORETO, Maria Antonietta;TARDELLA, Paolo Antonio
2006
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. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
