Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions

被引:226
|
作者
Groaning, MD [1 ]
Meyers, AI [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4020(00)00926-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral non-racemic bicyclic lactam has proven to be an exceptionally versatile chiral template for the asymmetric construction of a variety of optically pure compounds. Those lactams derived from keto acids have been applied to the synthesis of a host of natural products and pharmacologically interesting heterocycles and carbocycles. A variety of mechanistic questions regarding facial stereo-control have been investigated using the chiral template as the key probe. However, further elucidation of the subtle mechanistic principles involved await further study.
引用
收藏
页码:9843 / 9873
页数:31
相关论文
共 50 条
  • [41] Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine.
    Roussi, F
    Bonin, M
    Chiaroni, A
    Micouin, L
    Riche, C
    Husson, HP
    TETRAHEDRON LETTERS, 1999, 40 (19) : 3727 - 3730
  • [42] Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis
    Tiecco, Marcello
    Testaferri, Lorenzo
    Santi, Claudio
    Tomassini, Cristina
    Marini, Francesca
    Bagnoli, Luana
    Temperini, Andrea
    2002, Wiley-VCH Verlag (08)
  • [43] Enzymatic synthesis of chiral, non-racemic phosphoryl compounds
    Kielbasinski, P
    Mikolajczyk, M
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 109 (1-4) : 497 - 500
  • [44] Efficient preparation of chiral non-racemic sulfur compounds
    Minville, Joannie
    Girardin, Melina
    Spino, Claude
    CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (09) : 603 - 618
  • [45] Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis
    Tiecco, M
    Testaferri, L
    Santi, C
    Tomassini, C
    Marini, F
    Bagnoli, L
    Temperini, A
    CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (05) : 1118 - 1124
  • [46] DIASTEREOSELECTIVE BIS-ALKYLATION OF CHIRAL NON-RACEMIC ALPHA,BETA-UNSATURATED GAMMA-LACTAMS
    BAUSSANNE, I
    CHIARONI, A
    HUSSON, HP
    RICHE, C
    ROYER, J
    TETRAHEDRON LETTERS, 1994, 35 (23) : 3931 - 3934
  • [47] Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates
    Mumtaz, Salma
    Cano, Israel
    Mumtaz, Nargis
    Abbas, Ahmed
    Dupont, Jairton
    Gondal, Humaira Yasmeen
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2018, 20 (32) : 20821 - 20826
  • [48] Chiral bicyclic lactams: Useful precursors and templates for asymmetric syntheses
    Meyers, AI
    Brengel, GP
    CHEMICAL COMMUNICATIONS, 1997, (01) : 1 - 8
  • [49] Asymmetric routes to the trisporic acids via chiral bicyclic lactams
    Reeder, MR
    Meyers, AI
    TETRAHEDRON LETTERS, 1999, 40 (16) : 3115 - 3118
  • [50] An Efficient Synthesis of Chiral Non-Racemic Hydroxyalkanoic Acids by Olefin Cross-Metathesis Reactions
    Asaro, Fioretta
    Drioli, Sara
    Forzato, Cristina
    Nitti, Patrizia
    CHEMISTRYSELECT, 2018, 3 (47): : 13372 - 13376