Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinylphosphonates

作者: Dae Young Kim , Dae Yong Rhie

DOI: 10.1016/S0040-4020(97)00880-6

关键词:

摘要: Abstract A new synthesis of α-aminoalkylphosphonates from vinylphosphonates is described. The synthetic method involves the aziridination using PhI=NTs in presence copper catalyst. Aziridinylphosphonates thus obtained furnish corresponding α-amino-alkylphosphonates good overall yields after catalytic hydrogenation.

参考文章(65)
David A. Evans, Margaret M. Faul, Mark T. Bilodeau, Benjamin A. Anderson, David M. Barnes, Bis(oxazoline)-copper complexes as chiral catalysts for the enantioselective aziridination of olefins Journal of the American Chemical Society. ,vol. 115, pp. 5328- 5329 ,(1993) , 10.1021/JA00065A068
Pedro J. Perez, M. Brookhart, J. L. Templeton, A copper(I) catalyst for carbene and nitrene transfer to form cyclopropanes, cyclopropenes, and aziridines Organometallics. ,vol. 12, pp. 261- 262 ,(1993) , 10.1021/OM00026A007
A.R Sardarian*, B Kaboudin, A Novel Synthesis of Diethyl 1-Aminoarylmethylphosphonates on the Surface of Alumina Tetrahedron Letters. ,vol. 38, pp. 2543- 2546 ,(1997) , 10.1016/S0040-4039(97)00396-1
Hiroaki Sasai, Shigeru Arai, Yoshihiro Tahara, Masakatsu Shibasaki, Catalytic Asymmetric Synthesis of .alpha.-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes Journal of Organic Chemistry. ,vol. 60, pp. 6656- 6657 ,(1995) , 10.1021/JO00126A003
Gilbert Lavielle, Patrick Hautefaye, Corinne Schaeffer, Jean A. Boutin, Claude A. Cudennec, Alain Pierre, New .alpha.-amino phosphonic acid derivatives of vinblastine: chemistry and antitumor activity Journal of Medicinal Chemistry. ,vol. 34, pp. 1998- 2003 ,(1991) , 10.1021/JM00111A012
Philippe Coutrot, Abdelaziz Elgadi, Claude Grison, Highly Functionalized Aziridines II; A Facile Synthesis of Diethyl Aziridinylphosphonates and 2-Chloroaziridinylphosphonates HETEROCYCLES. ,vol. 28, pp. 1179- 1192 ,(1989) , 10.3987/COM-88-S147
F. R. Atherton, M. J. Hall, C. H. Hassall, R. W. Lambert, W. J. Lloyd, P. S. Ringrose, Phosphonopeptides as Antibacterial Agents: Mechanism of Action of Alaphosphin Antimicrobial Agents and Chemotherapy. ,vol. 15, pp. 696- 705 ,(1979) , 10.1128/AAC.15.5.696
Janusz Kowalik, Jan Zygmunt, Przemysław Mastalerz, Determination of absolute configuration of optically active 1-aminoalkanephosphonic acids by chemical correlations Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 18, pp. 393- 396 ,(1983) , 10.1080/03086648308076048