A VERSATILE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO ALPHA-ALKYL-PHOSPHONIC ACIDS OF HIGH ENANTIOMERIC PURITY

被引:117
作者
HANESSIAN, S
BENNANI, YL
机构
关键词
D O I
10.1016/S0040-4039(00)97092-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general protocol for the synthesis of α-amino-α- alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from (R,R)- and (S,S)-1,2-diaminocyclohexane. © 1990.
引用
收藏
页码:6465 / 6468
页数:4
相关论文
共 36 条
[1]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[2]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].
ATHERTON, FR ;
HASSALL, CH ;
LAMBERT, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40
[3]   PHOSPHINIC ACID DIPEPTIDE ANALOGS - POTENT, SLOW-BINDING INHIBITORS OF ASPARTIC PEPTIDASES [J].
BARTLETT, PA ;
KEZER, WB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4282-4283
[4]   DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES [J].
BARTLETT, PA ;
MCLAREN, KL .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 33 (1-2) :1-14
[5]   PHOSPHONAMIDATES AS TRANSITION-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].
BARTLETT, PA ;
MARLOWE, CK .
BIOCHEMISTRY, 1983, 22 (20) :4618-4624
[6]   STRUCTURE OF A CHIRAL CHLOROPROPYL BICYCLIC PHOSPHONAMIDE [J].
BELANGERGARIEPY, F ;
BENNANI, YL ;
HANESSIAN, S ;
BRISSE, F .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :289-291
[7]   STRUCTURE OF A CHIRAL AZIDOPROPYL BICYCLIC PHOSPHONAMIDE [J].
BENNANI, YL ;
BELANGERGARIEPY, F ;
HANESSIAN, S .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1990, 46 :653-656
[8]   SOLUTION AND SOLID-STATE STRUCTURE OF A PHOSPHORUS-STABILIZED CARBANION [J].
DENMARK, SE ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :864-866
[9]   OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].
DHAWAN, B ;
REDMORE, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144
[10]   PREPARATION, SEPARATION, AND CHARACTERIZATION OF LEL3-ISOMERS AND OB3-ISOMERS OF TRIS(TRANS-1,2-CYCLOHEXANEDIAMINE) RHODIUM (III) COMPLEXES [J].
GALSBOL, F ;
STEENBOL, P ;
SORENSEN, BS .
ACTA CHEMICA SCANDINAVICA, 1972, 26 (09) :3605-3611