α‐Amino‐α‐vinyl‐γ‐butyrolactone Derivatives from α‐{[(Trimethylsilyl)methyl]alkylidene}‐γ‐butyrolactones

作者: Marinella Capuzzi , Augusto Gambacorta , Tecla Gasperi , M. Antonietta Loreto , P. Antonio Tardella

DOI: 10.1002/EJOC.200600540

关键词: ChemistryTrisStereochemistryAziridineRing (chemistry)TrimethylsilylStereoselectivityPalladium

摘要: N-Protected α-amino-α-vinyl-γ-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO2Et to novel silylated α-ylidene-γ-butyrolactones 2, through ring opening intermediate aziridine and loss trimethylsilyl group. The stereoselective synthesis compounds cross-coupling reactions between α-[(triflyloxy)ylidene]-γ-butyrolactones 3 tris[(trimethylsilyl)methyl]aluminum, is also described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

参考文章(34)
Richard C. D. Brown, Carole J. R. Bataille, Gordon Bruton, Jeremy D. Hinks, Nigel A. Swain, C−H Insertion Approach to the Synthesis of endo,exo-Furofuranones: Synthesis of (±)-Asarinin, (±)-Epimagnolin A, and (±)-Fargesin Journal of Organic Chemistry. ,vol. 66, pp. 6719- 6728 ,(2001) , 10.1021/JO015829Q
Maria Antonietta Loreto, Paolo A. Tardella, Daniela Tofani, Stereochemistry in reactions of chiral cyclic allylsilanes with (ethoxycarbonyl)nitrene. A new route to chiral N-substituted allylamines Tetrahedron Letters. ,vol. 36, pp. 8295- 8298 ,(1995) , 10.1016/0040-4039(95)01734-Y
M.Antonietta Loreto, Clinio Pompili, Paolo A Tardella, α-Methylene β-amino phosphonic ester derivatives by amination of (1-trimethylsilanylmethyl-vinyl) phosphonic esters Tetrahedron. ,vol. 57, pp. 4423- 4427 ,(2001) , 10.1016/S0040-4020(01)00311-8
S. Jane deSolms, Elizabeth A. Giuliani, Samuel L. Graham, Kenneth S. Koblan, Nancy E. Kohl, Scott D. Mosser, Allen I. Oliff, David L. Pompliano, Elaine Rands, Thomas H. Scholz, Catherine M. Wiscount, Jackson B. Gibbs, Robert L. Smith, N-Arylalkyl Pseudopeptide Inhibitors of Farnesyltransferase Journal of Medicinal Chemistry. ,vol. 41, pp. 2651- 2656 ,(1998) , 10.1021/JM9800907
Laurent Chabaud, Philippe James, Yannick Landais, Allylsilanes in Organic Synthesis − Recent Developments European Journal of Organic Chemistry. ,vol. 2004, pp. 3173- 3199 ,(2004) , 10.1002/EJOC.200300789
J.A Olsen, R Severinsen, T.B Rasmussen, M Hentzer, M Givskov, J Nielsen, Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers Bioorganic & Medicinal Chemistry Letters. ,vol. 12, pp. 325- 328 ,(2002) , 10.1016/S0960-894X(01)00756-9
Peter J. Stang, Warren L. Treptow, Synthesis and antitumor activity of simple vinyl and .alpha.-methylene-.gamma.-butyrolactone sulfonate esters and silyl enol ethers Journal of Medicinal Chemistry. ,vol. 24, pp. 468- 472 ,(1981) , 10.1021/JM00136A019
James R. Blanton, Robert E. Salley, Preparation and utilization of a macromolecular analog of N-tert-butyl-N-ethylamine as a reusable amide base Journal of Organic Chemistry. ,vol. 54, pp. 723- 726 ,(1989) , 10.1021/JO00264A045