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α‐Amino‐α‐vinyl‐γ‐butyrolactone Derivatives from α‐{[(Trimethylsilyl)methyl]alkylidene}‐γ‐butyrolactones
Author(s) -
Capuzzi Marinella,
Gambacorta Augusto,
Gasperi Tecla,
Loreto M. Antonietta,
Tardella P. Antonio
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600540
Subject(s) - chemistry , trimethylsilyl , aziridine , stereoselectivity , tris , ring (chemistry) , medicinal chemistry , organic chemistry , stereochemistry , catalysis , biochemistry
N ‐Protected α‐amino‐α‐vinyl‐γ‐butyrolactones 1 are obtained by the aza‐Michael‐type addition of NsONHCO 2 Et to novel silylated α‐ylidene‐γ‐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 α‐[(triflyloxy)ylidene]‐γ‐butyrolactones 3 and tris[(trimethylsilyl)methyl]aluminum, is also described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)