Intramolecular asymmetric Heck reactions: Evidence for dynamic kinetic resolution effects

被引：27
|
作者：
McDermott, Michael C.
Stephenson, G. Richard [1 ]
Hughes, David L.
Walkington, Andrew J.
机构：
[1] Univ E Anglia, Sch Chem Sci & Pharm, Wolfson Mat & Catalysis Ctr, Norwich NR4 7TJ, Norfolk, England
[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 14期
关键词：
D O I：
10.1021/ol0606132
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselectivity of the cyclization of 1 varies at different stages in the reaction. X-ray crystallography has shown that 1 exists as enantiomerically pure (M) and (P) chiral helical structures defined by the relative orientations of the arene, amide, and alkene. The relative rates of interconversion of the rotamers of 1 have been established, leading to mechanistic proposals to account for the variation of ee based on kinetic resolution effects.
引用
收藏
页码：2917 / 2920
页数：4
相关论文
共 50 条
  • [1] Mechanistic aspects of asymmetric intramolecular Heck reaction involving dynamic kinetic resolution: flexible conformation of the cyclohexenylidene-benzene system
    Hosoi, Shinzo
    Ozeki, Minoru
    Nakano, Masashi
    Arimitsu, Kenji
    Kajimoto, Tetsuya
    Kojima, Naoto
    Iwasaki, Hiroki
    Miura, Takuya
    Kimura, Hiroyuki
    Node, Manabu
    Yamashita, Masayuki
    TETRAHEDRON, 2015, 71 (15) : 2317 - 2326
  • [2] Monodentate phosphoramidites; versatile ligands in catalytic asymmetric intramolecular Heck reactions
    Imbos, R
    Minnaard, AJ
    Feringa, BL
    DALTON TRANSACTIONS, 2003, (10) : 2017 - 2023
  • [3] Sequential olefin metathesis - Intramolecular asymmetric Heck reactions in the synthesis of polycycles
    Lautens, M
    Zunic, V
    CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) : 399 - 407
  • [4] Recent advances in intramolecular kinetic resolution reactions
    Peng, Tianyu
    Li, Shixin
    Yang, Dongxu
    Wang, Linqing
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (13): : 3401 - 3428
  • [5] The development of the intramolecular asymmetric Heck reaction
    Guiry, PJ
    Kiely, D
    CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) : 781 - 794
  • [6] The asymmetric Heck and related reactions
    Mc Cartney, Dennis
    Guiry, Patrick J.
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5122 - 5150
  • [7] Intramolecular Heck reactions of bromopyrroles.
    Goodwin, TE
    Szwedo, DM
    Blair, AC
    Banwell, MG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U137 - U137
  • [8] Kinetic Isotope Effects in Asymmetric Reactions
    Giagou, Thomas
    Meyer, Matthew P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (35) : 10616 - 10628
  • [9] Ligand effects in the synthesis of N-heterocycles by intramolecular Heck reactions
    Cropper, EL
    White, AJP
    Ford, A
    Hii, KK
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04): : 1732 - 1735
  • [10] Kinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium-Catalyzed Asymmetric Hydroarylation
    Yang, Qingjing
    Wang, Yanbo
    Luo, Shihui
    Wang, Jun Joelle
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) : 5343 - 5347
12345