ASYMMETRIC-SYNTHESIS OF 1-AMINOALKYLPHOSPHONIC ACIDS

被引:15
作者
JACQUIER, R
LHASSANI, M
PETRUS, C
PETRUS, F
机构
[1] Laboratoire de synthése et d'études physicochimiques d'aminoacides et de peptides. U. A. C.N.R.S. 468. Université Monypellier II, Sciences et Techniques du Languedoc
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1993年 / 81卷 / 1-4期
关键词
(-) EPHEDRINE; CHLOROMETHYL PHOSPHONIC DICHLORIDE; 1,3,2-OXAZAPHOSPHOLANES; OPTICALLY ACTIVE (S) AND (R) 1-AMINOALKYLPHOSPHONIC ACIDS;
D O I
10.1080/10426509308034376
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric synthesis of Phe and Tyr phosphonic analogous has been achieved by diastereoselective alkylation of chiral 1,2,3-oxazaphospholanes, the latter being readily obtained from (-) ephedrine and chloromethylphosphonic dichloride.
引用
收藏
页码:83 / 87
页数:5
相关论文
共 10 条
[1]   1,3,2-OXAZAPHOSPHOLIDINES FROM (-)-EPHEDRINE - INTERMEDIATES FOR STEREOSPECIFIC SYNTHESIS OF OPTICALLY-ACTIVE DIALKYL ALKYLPHOSPHONOTHIOATES AND DIALKYL ALKYLPHOSPHONO-SELENOATES, TRIALKYL PHOSPHORO-THIOATES AND TRIALKYL PHOSPHONO-SELENOATES, DIALKYL METHYLPHOSPHONATES, AND TRIALKYL PHOSPHATES [J].
COOPER, DB ;
HALL, CR ;
HARRISON, JM ;
INCH, TD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (17) :1969-1980
[2]  
COOPER DB, 1974, TETRAHEDRON LETT, V31, P2697
[3]   ASYMMETRIC ELECTROPHILIC AMINATION OF CHIRAL PHOSPHORUS-STABILIZED ANIONS [J].
DENMARK, SE ;
CHATANI, N ;
PANSARE, SV .
TETRAHEDRON, 1992, 48 (11) :2191-2208
[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]   A VERSATILE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO ALPHA-ALKYL-PHOSPHONIC ACIDS OF HIGH ENANTIOMERIC PURITY [J].
HANESSIAN, S ;
BENNANI, YL .
TETRAHEDRON LETTERS, 1990, 31 (45) :6465-6468
[6]   STUDIES TOWARD A MODEL FOR PREDICTING THE DIASTEREOSELECTIVITY IN THE ELECTROPHILIC AMINATION OF CHIRAL 1,3,2-OXAZAPHOSPHOLANES [J].
JOMMI, G ;
MIGLIERINI, G ;
PAGLIARIN, R ;
SELLO, G ;
SISTI, M .
TETRAHEDRON, 1992, 48 (35) :7275-7288
[7]   A SIMPLE AND GENERAL-METHOD FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS [J].
MAURY, C ;
ROYER, J ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1992, 33 (41) :6127-6130
[8]  
Pilk J., 1943, U. S. Patent, Patent No. 2328358
[9]  
STING M, 1990, SYNTHESIS-STUTTGART, P132
[10]   PEPTIDES CONTAINING AMINOPHOSPHONIC ACIDS .2. SYNTHESIS OF TRIPEPTIDE ANALOGS [J].
YAMAUCHI, K ;
IMOTO, M ;
KINOSHIT.M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (08) :2531-+