Asymmetric synthesis of aziridine 2-phosphonates and azirinyl phosphonates from enantiopure sulfinimines

被引:72
作者
Davis, FA [1 ]
McCoull, W [1 ]
机构
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
关键词
D O I
10.1016/S0040-4039(98)02331-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiopure sulfinimine (S)-4 was employed in a Darzens-type synthesis of aziridine 2-phosphonates (-)-7/(+)-8 which were transformed into alpha-amino phosphonates (S)-11/(R)-12 and the first enantiopure examples of azirinyl phosphonates 13-15. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:249 / 252
页数:4
相关论文
共 28 条
[1]   PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
NATURE, 1978, 272 (5648) :56-58
[2]   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
[3]   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
[4]   POTENT INHIBITION OF PEPSIN AND PENICILLOPEPSIN BY PHOSPHORUS-CONTAINING PEPTIDE ANALOGS [J].
BARTLETT, PA ;
HANSON, JE ;
GIANNOUSIS, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6268-6274
[5]   SYNTHESIS OF NOVEL N-PHOSPHONOALKYL DIPEPTIDE INHIBITORS OF HUMAN COLLAGENASE [J].
BIRD, J ;
DEMELLO, RC ;
HARPER, GP ;
HUNTER, DJ ;
KARRAN, EH ;
MARKWELL, RE ;
MILESWILLIAMS, AJ ;
RAHMAN, SS ;
WARD, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (01) :158-169
[6]   ALKYLATION OF CHIRAL PHOSPHONOGLYCINE EQUIVALENTS - ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES [J].
CABELLA, G ;
JOMMI, G ;
PAGLIARIN, R ;
SELLO, G ;
SISTI, M .
TETRAHEDRON, 1995, 51 (06) :1817-1826
[7]   HIGHLY FUNCTIONALIZED AZIRIDINES .2. A FACILE SYNTHESIS OF DIETHYL AZIRIDINYLPHOSPHONATES AND 2-CHLOROAZIRIDINYLPHOSPHONATES [J].
COUTROT, P ;
ELGADI, A ;
GRISON, C .
HETEROCYCLES, 1989, 28 (02) :1179-1192
[8]   ASYMMETRIC-SYNTHESIS OF 2H-AZIRINES - FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CYTOTOXIC ANTIBIOTIC (R)-(-)-DYSIDAZIRINE [J].
DAVIS, FA ;
REDDY, GV ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3651-3652
[9]   Asymmetric synthesis of beta-substituted alpha-amino acids using 2H-azirine-2-carboxylate esters. Synthesis of 3,3-disubstituted aziridine-2-carboxylate esters [J].
Davis, FA ;
Liang, CH ;
Liu, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3796-3797
[10]   An efficient synthesis of (S)-(+)-ethyl beta-amino-3-pyridinepropanoate using enantiopure sulfinimines [J].
Davis, FA ;
Szewczyk, JM ;
Reddy, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2222-2225