ASYMMETRIC SYNTHESIS OF ALPHA AMINOPHOSPHONIC ACIDS .4. ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE PHOSPHONIC ANALOGS OF GLUTAMIC-ACID AND PROLINE

被引：58
|
作者：
GROTH, U [1 ]
RICHTER, L [1 ]
SCHOLLKOPF, U [1 ]
机构：
[1] UNIV GOTTINGEN,INST ORGAN CHEM,TAMMANNSTR 2,W-3400 GOTTINGEN,GERMANY
来源：
TETRAHEDRON | 1992年 / 48卷 / 01期
关键词：
D O I：
10.1016/S0040-4020(01)80584-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Michael addition of the metallated camphor derivatives 2 to vinylogous esters and subsequential hydrolysis afforded phosphonic analogues of glutamic acid. The enantiomerically pure lactam 6 was reduced by LiBH4/BF3.OEt2 to phosphoproline 7.
引用
收藏
页码：117 / 122
页数：6
相关论文
共 50 条
  • [1] ASYMMETRIC-SYNTHESIS OF HIGHLY ENANTIOMERICALLY PURE ALPHA-HYDROXYACIDS
    ELIEL, EL
    LYNCH, JE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 183 (MAR): : 19 - ORGN
  • [2] NUCLEOPHILIC ADDITIONS TO N-GLYCOSYLNITRONES .4. ASYMMETRIC-SYNTHESIS OF N-HYDROXY-ALPHA-AMINOPHOSPHONIC AND ALPHA-AMINOPHOSPHONIC ACIDS
    HUBER, R
    VASELLA, A
    HELVETICA CHIMICA ACTA, 1987, 70 (06) : 1461 - 1476
  • [3] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS .2. ASYMMETRIC ADDITION OF A CHIRAL CYCLIC PHOSPHITE TO A CYCLIC IMINE - SYNTHESIS OF PHOSPHONIC ACID ANALOGS OF D-PENICILLAMINE AND L-PENICILLAMINE
    HOPPE, I
    SCHOLLKOPF, U
    NIEGER, M
    EGERT, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (12): : 1067 - 1068
  • [4] ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE AND DIVERSELY FUNCTIONALIZED CYCLOPROPANES
    HANESSIAN, S
    ANDREOTTI, D
    GOMTSYAN, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) : 10393 - 10394
  • [5] ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES AS REAGENTS AND AUXILIARIES FOR ASYMMETRIC-SYNTHESIS
    CHU, KS
    NEGRETE, GR
    KONOPELSKI, JP
    LAKNER, FJ
    WOO, NT
    OLMSTEAD, MM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1800 - 1812
  • [6] A SIMPLE AND GENERAL-METHOD FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS
    MAURY, C
    ROYER, J
    HUSSON, HP
    TETRAHEDRON LETTERS, 1992, 33 (41) : 6127 - 6130
  • [7] ASYMMETRIC-SYNTHESIS OF BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES
    KONOPELSKI, JP
    CHU, SC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 191 - ORGN
  • [8] ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-PHOSPHONAMIDES, PHOSPHONATES AND PHOSPHONIC-ACIDS
    BLAZIS, VJ
    KOELLER, KJ
    SPILLING, CD
    TETRAHEDRON-ASYMMETRY, 1994, 5 (04) : 499 - 502
  • [9] THE ASYMMETRIC-SYNTHESIS OF GAMMA-SUBSTITUTED GLUTAMIC-ACID DERIVATIVES VIA A GLUTAMIC-ACID GAMMA-ENOLATE SYNTHON
    DELBOSCO, M
    JOHNSTONE, ANC
    BAZZA, G
    LOPATRIELLO, S
    NORTH, M
    TETRAHEDRON, 1995, 51 (31) : 8545 - 8554
  • [10] NUCLEOPHILIC ADDITIONS TO N-GLYCOSYLNITRONES - ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS
    HUBER, R
    KNIERZINGER, A
    OBRECHT, JP
    VASELLA, A
    HELVETICA CHIMICA ACTA, 1985, 68 (06) : 1730 - 1747
12345