Asymmetric 1,3-dipolar cycloadditions of cyclic stabilized ylides derived from chiral 1,2-amino alcohols

被引:93
作者
Bonin, Martine [1 ]
Chauveau, Ariane [1 ]
Micouin, L. [1 ]
机构
[1] Univ Paris 05, CNRS, UMR 8638, Lab Chim Therapeut,Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
关键词
cycloadditions; ylides; stereoselective synthesis; heterocycles; multicomponent reactions;
D O I
10.1055/s-2006-949626
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of structurally similar chiral non-racemic azomethine ylides, nitrones and azomethine imines derived from 1,2-aminol alcohols in asymmetric dipolar cycloadditions is reviewed. This general survey underlines the great synthetic potential of dipolar cycloadditions, especially in a diversity-oriented approach and enables a direct comparison of the reactivity of apparently closely related reactive systems.
引用
收藏
页码:2349 / 2363
页数:15
相关论文
共 66 条
  • [1] A concise asymmetric synthesis of the ADE fragment of nakadomarin
    Ahrendt, KA
    Williams, RM
    [J]. ORGANIC LETTERS, 2004, 6 (24) : 4539 - 4541
  • [2] 1,3-Dipolar cycloadditions to unsymmetrical ketone-derived chiral stabilized azomethine ylides: Strategies for the synthesis of highly substituted amino acids
    Aldous, DJ
    Drew, MGB
    Draffin, WN
    Hamelin, EMN
    Harwood, LM
    Thurairatnam, S
    [J]. SYNTHESIS-STUTTGART, 2005, (19): : 3271 - 3278
  • [3] Aldous DJ, 2001, SYNLETT, P1841
  • [4] Aldous DJ, 2001, SYNLETT, P1836
  • [5] Carbamate derived stable precursors for generating chiral azomethine ylids under mild conditions.
    Alker, D
    Harwood, LM
    Williams, CE
    [J]. TETRAHEDRON, 1997, 53 (37) : 12671 - 12678
  • [6] Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis
    Alker, D
    Hamblett, G
    Harwood, LM
    Robertson, SM
    Watkin, DJ
    Williams, CE
    [J]. TETRAHEDRON, 1998, 54 (22) : 6089 - 6098
  • [7] Cycloadditions of aromatic imines to enantiomerically pure stabilized azomethine ylids:: Construction of threo (2S,3R)-3-aryl-2,3-diamino acids
    Alker, D
    Harwood, LM
    Williams, CE
    [J]. TETRAHEDRON LETTERS, 1998, 39 (5-6) : 475 - 478
  • [8] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDS - COMPLETING THE MEMORY RELAY
    ANSLOW, AS
    HARWOOD, LM
    PHILLIPS, H
    WATKIN, D
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (10) : 997 - 1000
  • [9] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDES - A CHIRAL MEMORY RELAY SYSTEM
    ANSLOW, AS
    HARWOOD, LM
    PHILLIPS, H
    WATKIN, D
    WONG, LF
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1343 - 1358
  • [10] DEVELOPMENT OF A CHIRAL STABILIZED AZOMETHINE YLID - A CHIRAL RELAY SYSTEM
    ANSLOW, AS
    HARWOOD, LM
    PHILLIPS, H
    WATKIN, D
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 169 - 172