Regio- and stereoselective synthesis of 2-amino-1-hydroxy-2-aryl ethylphosphonic esters

被引:45
作者
Cristau, HJ
Pirat, JL
Drag, M
Kafarski, P
机构
[1] Ecole Natl Super Chim Montpellier, CNRS, UMR 5076, Chim Organ Lab, F-34296 Montpellier 5, France
[2] Univ Technol Wroclaw, Inst Organ Chem, PL-50370 Wroclaw, Poland
关键词
2-amino-1-hydroxy-2-aryl ethylphosphonic esters; beta-aminophosphonic esters; alpha-hydroxyphosphonic esters; ammonolysis; 1,2-epoxyphosphonic esters;
D O I
10.1016/S0040-4039(00)01722-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly regio- and diastereoselective synthesis of 2-amino-1-hydroxy-2-aryl ethylphosphonic esters was achieved by opening trans 1,2-epoxy-2-aryl ethylphosphonic esters with 28% NH3(aq.) in methanol. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码:9781 / 9785
页数:5
相关论文
共 14 条
[1]   Dioxirane oxidation of substituted vinylphosphonates: a novel efficient route to 1,2-epoxyalkylphosphonates [J].
Cristau, HJ ;
Mbianda, XY ;
Geze, A ;
Beziat, Y ;
Gasc, MB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 571 (02) :189-193
[2]   ALPHA-SUBSTITUTED PHOSPHONATES .39. METHANE-DIPHOSPHONIC ESTERS BY UV-INDUCED MICHAELIS-BECKER-REACTION [J].
CZEKANSKI, T ;
GROSS, H ;
COSTISELLA, B .
JOURNAL FUR PRAKTISCHE CHEMIE, 1982, 324 (04) :537-544
[3]  
DELLARIA F, 1990, J MED CHEM, P534
[4]   OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].
DHAWAN, B ;
REDMORE, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144
[5]   PHOSPHONIC ACIDS AND ESTERS .20. PREPARATION AND RING-OPENING REACTIONS OF ALPHA,BETA-EPOXYALKYLPHOSPHONATES AND BETA,GAMMA-EPOXYALKYLPHOSPHONATES . PROTON MAGNETIC RESONANCE SPECTRA OF VICINALLY SUBSTITUTED ETHYL- AND PROPYLPHOSPHONATES [J].
GRIFFIN, CE ;
KUNDU, SK .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1532-&
[6]   BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].
KAFARSKI, P ;
LEJCZAK, B .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215
[7]  
Lindlar H., 1966, Org. Synth., V46, P89, DOI [10.15227/orgsyn.046.0089, DOI 10.15227/ORGSYN.046.0089]
[8]  
MIKOLAJCZYK M, 1976, SYNTHESIS-STUTTGART, P396
[9]   PEPTIDE-BOND FORMATION VIA CATALYTIC ANTIBODIES - SYNTHESIS OF A NOVEL PHOSPHONATE DIESTER HAPTEN [J].
SMITH, AB ;
TAYLOR, CM ;
BENKOVIC, SJ ;
HIRSCHMANN, R .
TETRAHEDRON LETTERS, 1994, 35 (37) :6853-6856
[10]   NEW HYBRID TRANSITION-STATE ANALOG INHIBITORS OF HIV PROTEASE WITH PERIPHERAL C2-SYMMETRY [J].
STOWASSER, B ;
BUDT, KH ;
LI, JQ ;
PEYMAN, A ;
RUPPERT, D .
TETRAHEDRON LETTERS, 1992, 33 (44) :6625-6628