Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives

被引：0
|
作者：
E. G. Mamedov
E. I. Klabunovskii
机构：
[1] National Academy of Sciences of Azerbaidjan,Institute of Petrochemical Processes
[2] Russian Academy of Sciences,Zelinskii Institute of Organic Chemistry
来源：
Russian Journal of Organic Chemistry | 2008年 / 44卷
关键词：
Cyclopentadiene; Alder Reaction; Optical Yield; Menthyl; Chiral Catalyst;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
The review discusses available data on asymmetric Diels-Alder reactions of cyclopentadiene, which were published in the past decade. Both noncatalytic and catalytic (in the presence of achiral and chiral catalysts) versions of these reactions are considered. Effects of various factors on the chemical and optical yields, stereoselectivity, and optical purity of the Diels-Alder adducts are analyzed. Prospects in the development of this field of organic chemistry are examined.
引用
收藏
页码：1097 / 1120
页数：23
相关论文
共 50 条
  • [1] Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives
    Mamedov, E. G.
    Klabunovskii, E. I.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (08) : 1097 - 1120
  • [2] Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones
    Brimble, MA
    McEwan, JF
    Turner, P
    TETRAHEDRON-ASYMMETRY, 1998, 9 (07) : 1239 - 1255
  • [3] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL (E)-2-CYANOCINNAMATES WITH CYCLOPENTADIENE
    CATIVIELA, C
    MAYORAL, JA
    AVENOZA, A
    PEREGRINA, JM
    LAHOZ, FJ
    GIMENO, S
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17): : 4664 - 4669
  • [4] Synthesis and properties of chiral N,N-maleoyl derivatives and Diels-Alder reactions with cyclopentadiene
    Bodtke, A
    Otto, HH
    PHARMAZIE, 2005, 60 (11): : 803 - 813
  • [5] ALPO4-CATALYZED ASYMMETRIC DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH CHIRAL ACRYLATES
    CATIVIELA, C
    FRAILE, JM
    GARCIA, JI
    MAYORAL, JA
    CAMPELO, JM
    LUNA, D
    MARINAS, JM
    TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2507 - 2512
  • [6] ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ALKOXYCYCLOHEXADIENES
    BIRD, CW
    LEWIS, A
    TETRAHEDRON LETTERS, 1989, 30 (45) : 6227 - 6228
  • [7] Synthesis of chiral bis-thiazolines and asymmetric Diels-Alder reactions
    Nishio, T
    Kodama, Y
    Tsurumi, Y
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) : 1449 - 1450
  • [8] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL ACRYLATES OF CHOLIC-ACID DERIVATIVES
    PACKIARAJAN, M
    MAITRA, U
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02): : 364 - 369
  • [9] Chiral anthracenes as a Diels-Alder/retro Diels-Alder template in asymmetric synthesis.
    Sanyal, A
    Snyder, JK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U121 - U121
  • [10] Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives
    Zhang, Ze
    Peng, Zhi-Wei
    Hao, Ming-Feng
    Gao, Jian-Gang
    SYNLETT, 2010, (19) : 2895 - 2898
12345