1,3-Dipolar cycloadditions to unsymmetrical ketone-derived chiral stabilized azomethine ylides: Strategies for the synthesis of highly substituted amino acids

被引：19
|
作者：
Aldous, DJ
Drew, MGB
Draffin, WN
Hamelin, EMN
Harwood, LM
Thurairatnam, S
机构：
[1] Univ Reading, Sch Chem, Reading RG6 6AD, Berks, England
[2] Rhone Poulenc Rorer Ltd, Dagenham RM10 7XS, Essex, England
来源：
SYNTHESIS-STUTTGART | 2005年 / 19期
关键词：
azomethine ylide; beta-hydroxy-alpha-amino acid; proline; intramolecular; cycloaddition;
D O I：
10.1055/s-2005-918487
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report herein, the first generation of unsymmetrical ketone-derived chiral stabilized azomethine ylides. Intrairiolecular and intermolecular cycloaddition strategies have been utilized to synthesize both an enantiornerically pure bicyclic proline derivative and an enantionierically pure beta-hydroxy-alpha-amino acid.
引用
收藏
页码：3271 / 3278
页数：8
相关论文
共 50 条
  • [1] AUXILIARY CONTROLLED 1,3-DIPOLAR CYCLOADDITIONS OF CHIRAL STABILIZED AZOMETHINE YLIDES
    GARNER, P
    DOGAN, O
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01): : 4 - 6
  • [2] AUXILIARY CONTROLLED 1,3-DIPOLAR CYCLOADDITIONS OF CHIRAL AZOMETHINE YLIDES
    GARNER, P
    DOGAN, O
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 142 - ORGN
  • [3] DOUBLE DIASTEREOSELECTIVITY OF 1,3-DIPOLAR CYCLOADDITIONS OF SUBSTITUTED CYCLIC AZOMETHINE YLIDES
    LAKHLIFI, T
    SEDQUI, A
    FATHI, T
    LAUDE, B
    ROBERT, JF
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (06): : 1417 - 1423
  • [4] 1,3-DIPOLAR CYCLOADDITIONS OF SOME AZOMETHINE YLIDES TO THIOKETONES
    MLOSTON, G
    SKRZYPEK, Z
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1990, 99 (03): : 167 - 170
  • [5] Nonstereospecific 1,3-dipolar cycloadditions of azomethine ylides and enamines
    Böhm, T
    Weber, A
    Sauer, J
    TETRAHEDRON, 1999, 55 (31) : 9535 - 9558
  • [6] Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions of Azomethine Ylides
    Cayuelas, Alberto
    Larranaga, Olatz
    Selva, Veronica
    Najera, Carmen
    Akiyama, Takahiko
    Sansano, Jose M.
    de Cozar, Abel
    Miranda, Jose I.
    Cossio, Fernando P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (32) : 8092 - 8097
  • [7] Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted α-methylene-γ-lactones
    Castulík, J
    Marek, J
    Mazal, C
    TETRAHEDRON, 2001, 57 (39) : 8339 - 8347
  • [8] Asymmetric 1,3-dipolar cycloadditions of cyclic stabilized ylides derived from chiral 1,2-amino alcohols
    Bonin, Martine
    Chauveau, Ariane
    Micouin, L.
    SYNLETT, 2006, (15) : 2349 - 2363
  • [9] THE SYNTHESIS OF AMINO-ACIDS BY 1,3-DIPOLAR CYCLO-ADDITIONS OF AZOMETHINE YLIDES
    KRAUS, GA
    NAGY, JO
    TETRAHEDRON, 1985, 41 (17) : 3537 - 3545
  • [10] 1,3-DIPOLAR CYCLOADDITIONS OF PHENANTHRIDINIUM-BASED AZOMETHINE YLIDES
    DOSTAL, J
    POTACEK, M
    HUMPA, O
    MAREK, J
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1994, 103 (7-8): : 343 - 348
12345