AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS

被引:117
作者
BALDWIN, JE [1 ]
SPIVEY, AC [1 ]
SCHOFIELD, CJ [1 ]
SWEENEY, JB [1 ]
机构
[1] OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)87968-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleophilic ring opening of optically active N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents has been investigated as a method of preparation of optically active amino acids.
引用
收藏
页码:6309 / 6330
页数:22
相关论文
共 53 条
  • [1] ARMSTRONG A, 1988, TETRAHEDRON LETT, V29, P1483
  • [2] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE
    ARNOLD, LD
    MAY, RG
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2237 - 2241
  • [3] CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS
    ARNOLD, LD
    DROVER, JCG
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4649 - 4659
  • [4] CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES
    ARNOLD, LD
    KALANTAR, TH
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) : 7105 - 7109
  • [5] BAJGROWICZ JA, 1984, TETRAHEDRON LETT, V25, P2759, DOI 10.1016/S0040-4039(01)81283-1
  • [6] ORGANOCUPRATES MEDIATED CARBON-CARBON BOND FORMATION IN GAMMA-POSITION OF ALPHA-AMINO ESTERS WITHOUT RACEMIZATION
    BAJGROWICZ, JA
    ELHALLAOUI, A
    JACQUIER, R
    PIGIERE, C
    VIALLEFONT, P
    [J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2231 - 2234
  • [7] ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS
    BAJGROWICZ, JA
    ELHALLAOUI, A
    JACQUIER, R
    PIGIERE, C
    VIALLEFONT, P
    [J]. TETRAHEDRON, 1985, 41 (10) : 1833 - 1843
  • [8] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS
    BALDWIN, JE
    ADLINGTON, RM
    ROBINSON, NG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) : 153 - 155
  • [9] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
    BALDWIN, JE
    ADLINGTON, RM
    ONEIL, IA
    SCHOFIELD, C
    SPIVEY, AC
    SWEENEY, JB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1852 - 1854
  • [10] BALDWIN JE, 1990, TETRAHEDRON ASSYMETR, P881