A new method for the synthesis of N-protected β-amino-α-keto esters from fluoroalkanesulfonylazides and α-keto esters

作者: Shizheng Zhu , Guifang Jin , Yong Xu

DOI: 10.1016/S0040-4020(03)00622-7

关键词:

摘要: Abstract In the presence of a secondary amine, treatment α-keto esters with fluoroalkanesulfonyl azides at room temperature afforded N -sulfonyl protected β-amino-α-keto in good to excellent yields. This reaction provided novel, direct and convenient access from under mild conditions. However, β-ketoester enamines two products: -fluoroalkanesulfonyl amidines diazoacetate. The mechanism is discussed.

参考文章(15)
Yong Xu, Yanli Wang, Shizheng Zhu, Guangyu Zhu, Yisi Jia, Qichen Huang, Synthesis of N-(1,2,3,6-tetrahydropyridylidene)-fluoroalkanesulfonylamides from reactions of per(poly)fluoroalkanesulfonyl azides with 1,2-dihydropyridines Journal of Fluorine Chemistry. ,vol. 106, pp. 133- 138 ,(2000) , 10.1016/S0022-1139(00)00322-5
Yong Xu, Guolin Xu, Shizheng Zhu, Guangyu Zhu, Yisi Jia, Qichen Huang, Reactions of fluoroalkanesulfonyl azides with trimethylsilyl enol ethers Journal of Fluorine Chemistry. ,vol. 96, pp. 79- 85 ,(1999) , 10.1016/S0022-1139(99)00009-3
Shi-Zheng Zhu, Synthesis and reactions of fluoroalkanesulfonyl azides and N,N-dichlorofluoroalkanesulfonamides Journal of The Chemical Society-perkin Transactions 1. pp. 2077- 2081 ,(1994) , 10.1039/P19940002077
J. Bourgois, A. Mathieu, F. Texier, Thermolysis and photolysis of some 5‐amino‐4‐methoxycarbonyl‐Δ2‐1,2,3‐triazolines Journal of Heterocyclic Chemistry. ,vol. 21, pp. 513- 515 ,(1984) , 10.1002/JHET.5570210249
Marielle Paris, Jean-Alain Fehrentz, Annie Heitz, Jean Martinez, Synthesis of N-urethane protected α-alkyl-γ-amino-β-keto-esters from urethane N-carboxyanhydrides (UNCAs) Tetrahedron Letters. ,vol. 39, pp. 1569- 1572 ,(1998) , 10.1016/S0040-4039(98)00026-4
Michael R. Angelastro, Shujaath Mehdi, Joseph P. Burkhart, Norton P. Peet, Philippe Bey, Alpha-diketone and alpha-keto ester derivatives of N-protected amino acids and peptides as novel inhibitors of cysteine and serine proteinases. Journal of Medicinal Chemistry. ,vol. 33, pp. 11- 13 ,(1990) , 10.1021/JM00163A002
Amalia Cipollone, M. Antonietta Loreto, Lucio Pellacani, Paolo A. Tardella, Reaction of ethyl azidoformate with ketene silyl acetals Journal of Organic Chemistry. ,vol. 52, pp. 2584- 2586 ,(1987) , 10.1021/JO00388A044
Joseph P. Burkhart, Norton P. Peet, Philippe Bey, A novel method for the preparation of peptidyl α-keto esters Tetrahedron Letters. ,vol. 31, pp. 1385- 1388 ,(1990) , 10.1016/S0040-4039(00)88812-7
Norton P. Peet, Joseph P. Burkhart, Michael R. Angelastro, Eugene L. Giroux, Shujaath Mehdi, Philippe Bey, Michael Kolb, Bernhard Neises, Daniel Schirlin, Synthesis of peptidyl fluoromethyl ketones and peptidyl alpha-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G. Journal of Medicinal Chemistry. ,vol. 33, pp. 394- 407 ,(1990) , 10.1021/JM00163A063