Pauson-Khand cycloaddition reactions of chiral ynamides.: Observation of an unusual endo-addition with norbornadiene

被引:43
|
作者
Shen, LC [1 ]
Hsung, RP [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1016/j.tetlet.2003.10.064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pauson-K hand cycloadditions using chiral ynamides are achieved in modest to good yields with excellent regioselectivity and modest stereoselectivity. An unusual endo addition is found when using norbornadiene and substituted ynamides, leading to cycloadducts that were not observed in previous studies using ynamides or ynamines. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9353 / 9358
页数:6
相关论文
共 36 条
  • [1] A chiral allenic Pauson-Khand cycloaddition.
    Brummond, KM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U78 - U78
  • [2] Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes
    Pallerla, MK
    Fox, JM
    ORGANIC LETTERS, 2005, 7 (16) : 3593 - 3595
  • [3] Reversing the stereoselectivity of the intermolecular Pauson-Khand reaction:: Formation of endo-fused norbornadiene adducts
    Rios, R
    Pericàs, MA
    Moyano, A
    Maestro, MA
    Mahía, J
    ORGANIC LETTERS, 2002, 4 (07) : 1205 - 1208
  • [4] Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions.
    Montenegro, E
    Poch, M
    Moyano, A
    Pericas, MA
    Riera, A
    TETRAHEDRON, 1997, 53 (25) : 8651 - 8664
  • [5] Catalytic Asymmetric Synthesis of Chiral Propargylic Alcohols For the Intramolecular Pauson-Khand Cycloaddition
    Turlington, Mark
    Yue, Yang
    Yu, Xiao-Qi
    Pu, Lin
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (20): : 6941 - 6952
  • [6] Catalytic use of chiral phosphine ligands in asymmetric Pauson-Khand reactions
    Hiroi, K
    Watanabe, T
    Kawagishi, R
    Abe, I
    TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 797 - 808
  • [7] endo-selective intramolecular Pauson-Khand reactions of γ-oxygenated-α,β-unsaturated phenylsulfones
    Adrio, J
    Rivero, MR
    Carretero, JC
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (11) : 2435 - 2448
  • [8] ENANTIOSELECTIVE PAUSON-KHAND REACTIONS MEDIATED BY A CHIRAL AMINE N-OXIDE
    KERR, WJ
    KIRK, GG
    MIDDLEMISS, D
    SYNLETT, 1995, (10) : 1085 - &
  • [9] Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Alkynes: The Transannular Pauson-Khand Reaction
    Karabiyikoglu, Sedef
    Boon, Byron A.
    Merlic, Craig A.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15): : 7732 - 7744
  • [10] A Computational Study on the Role of Chiral N-Oxides in Enantioselective Pauson-Khand Reactions
    Fjermestad, Torstein
    Pericas, Miquel A.
    Maseras, Feliu
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (36) : 10050 - 10057