A simple and versatile method to determine the enantiomeric purity of Diels-Alder adducts

被引:7
作者
Hall, A
Harris, LD
Jones, CL
Jenkins, RL
Tomkinson, NCO
机构
[1] Univ Wales Coll Cardiff, Dept Chem, Cardiff CF10 3TB, S Glam, Wales
[2] GlaxoSmithKline Res & Dev Ltd, Welwyn Garden City AL6 9AR, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(02)02454-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The determination of the enantiomeric purity of Diels-Alder adducts derived from cyclopentadiene and a series of electron-deficient dienophiles is conveniently achieved by HPLC analysis on their 2,4-dinitrophenylhydrazine derivatives formed in one-pot directly from the cycloaddition reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:111 / 114
页数:4
相关论文
共 16 条
  • [1] AN EASY AND FAST WAY TO DETERMINE THE ENANTIOMERIC PURITY OF SUBSTITUTED CYCLANONES
    ALEXAKIS, A
    FRUTOS, JC
    MANGENEY, P
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2431 - 2434
  • [2] Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine
    Corey, EJ
    Shibata, T
    Lee, TW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) : 3808 - 3809
  • [3] CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS
    FURUTA, K
    SHIMIZU, S
    MIWA, Y
    YAMAMOTO, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1481 - 1483
  • [4] Design and development of highly effective lewis acid catalysts for enantioselective Diels-Alder reactions
    Huang, Y
    Iwama, T
    Rawal, VH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5950 - 5951
  • [5] MECHANISTIC STUDIES OF A CAB-CATALYZED ASYMMETRIC DIELS-ALDER REACTION
    ISHIHARA, K
    GAO, QZ
    YAMAMOTO, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10412 - 10413
  • [6] Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3
  • [7] π shielding in organic synthesis
    Jones, GB
    [J]. TETRAHEDRON, 2001, 57 (38) : 7999 - 8016
  • [8] JONES GB, 1995, SYNTHESIS-STUTTGART, P475
  • [9] Enantioselective cycloadditions catalyzed by face resolved arene chromium carbonyl complexes
    Jones, GB
    Guzel, M
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (12) : 2023 - 2026
  • [10] Ojima I., 2000, CATALYTIC ASYMMETRIC, V2nd