Generation of unnatural α,α-disubstituted amino acid derivatives from cyclic sulfamidates

被引：47
作者：
Boulton, LT [1 ]
Stock, HT [1 ]
Raphy, J [1 ]
Horwell, DC [1 ]
机构：
[1] Univ Cambridge, Parke Davis Neurosci Res Ctr, Cambridge CB2 2QB, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 11期
关键词：
D O I：
10.1039/a901667h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclic sulfamidates function as excellent precursors to a variety of unnatural alpha,alpha-disubstituted amino acid derivatives by ring opening with a suitable nucleophile. Addition of various nucleophiles to a sulfamidate derived from 2-methylserine is described.
引用
收藏
页码：1421 / 1429
页数：9
相关论文
共 37 条
  • [1] Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations
    Aguilera, B
    FernandezMayoralas, A
    Jaramillo, C
    [J]. TETRAHEDRON, 1997, 53 (16) : 5863 - 5876
  • [2] Synthesis of a thio-analogue of Lewis X by regioselective opening of cyclic sulfamidates
    Aguilera, B
    Fernández-Mayoralas, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2719 - 2723
  • [3] Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides
    Aguilera, B
    FernandezMayoralas, A
    [J]. CHEMICAL COMMUNICATIONS, 1996, (02) : 127 - 128
  • [4] THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN
    ALKER, D
    DOYLE, KJ
    HARWOOD, LM
    MCGREGOR, A
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 877 - 880
  • [5] 1,2,3-BENZOXATHIAZOLE 2,2-DIOXIDES - SYNTHESIS, MECHANISM OF HYDROLYSIS, AND REACTIONS WITH NUCLEOPHILES
    ANDERSEN, KK
    BRAY, DD
    CHUMPRADIT, S
    CLARK, ME
    HABGOOD, GJ
    HUBBARD, CD
    YOUNG, KM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6508 - 6516
  • [6] ACIDITY OF CYCLIC SULFAMATES - STUDY OF SUBSTITUTED 1,2,3-BENZOXATHIAZOLE 2,2-DIOXIDES AND THEORETICAL INVESTIGATION OF THE EFFECT OF CONFORMATION ON ACIDITY
    ANDERSEN, KK
    KOCIOLEK, MG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) : 2003 - 2007
  • [7] PD 176252 -: The first high affinity non-peptide gastrin-releasing peptide (BB2) receptor antagonist
    Ashwood, V
    Brownhill, V
    Higginbottom, M
    Horwell, DC
    Hughes, J
    Lewthwaite, RA
    McKnight, AT
    Pinnock, RD
    Pritchard, MC
    Suman-Chauhan, N
    Webb, C
    Williams, SC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (18) : 2589 - 2594
  • [8] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS
    BALDWIN, JE
    SPIVEY, AC
    SCHOFIELD, CJ
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 881 - 884
  • [9] Black T.H., 1983, ALDRICHIM ACTA, V16, P3
  • [10] THE ASYMMETRIC-SYNTHESIS OF NONPEPTIDE CCK-A RECEPTOR AGONISTS
    BURGAUD, BGM
    HORWELL, DC
    PRITCHARD, MC
    BERNAD, N
    MARTINEZ, J
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (05) : 1081 - 1084
1234