Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes

被引：49
|
作者：
Pallerla, MK [1 ]
Fox, JM [1 ]
机构：
[1] Univ Delaware, Dept Chem & Biochem, HC Brown & RB Wetherill Labs Chem, Newark, DE 19716 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 16期
关键词：
D O I：
10.1021/ol051456u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this Letter, it is demonstrated that the unusual reactivity of cyclopropenes can increase the scope and utility of intermolecular Paulson-Khand reactions. The well-defined chiral environment of cyclopropenes has a powerful influence on the diastereoselectivity of the reactions and leads to the production of a single cyclopentenone in each of the described cases. The cyclopropane ring strongly influences the stereochemistry of reactions at the enone, and the three-membered ring can subsequently be cleaved under mild conditions.
引用
收藏
页码：3593 / 3595
页数：3
相关论文
共 50 条
  • [21] Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions.
    Montenegro, E
    Poch, M
    Moyano, A
    Pericas, MA
    Riera, A
    TETRAHEDRON, 1997, 53 (25) : 8651 - 8664
  • [22] A pyridylsilyl group expands the scope of catalytic intermolecular Pauson-Khand reactions
    Itami, K
    Mitsudo, K
    Yoshida, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (18) : 3481 - 3484
  • [23] Stable catalyst for intermolecular Pauson-Khand reaction
    Arias, JL
    Cabrera, A
    Sharma, P
    Rosas, N
    Sampere, R
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 246 (1-2) : 237 - 241
  • [24] Intermolecular cobalt-mediated Pauson-Khand reactions in ionic liquids
    Becheanu, A
    Laschat, S
    SYNLETT, 2002, (11) : 1865 - 1867
  • [25] PuPHOS:: A synthetically useful chiral bidentate ligand for the intermolecular Pauson-Khand reaction
    Verdaguer, X
    Lledó, A
    López-Mosquera, C
    Maestro, MA
    Pericàs, MA
    Riera, A
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23): : 8053 - 8061
  • [26] When the Pauson-Khand and Pauson-Khand type reactions go awry:: a plethora of unexpected results
    Boñaga, LVR
    Krafft, ME
    TETRAHEDRON, 2004, 60 (44) : 9795 - 9833
  • [27] Microwave promoted Pauson-Khand reactions
    Iqbal, M
    Vyse, N
    Dauvergne, J
    Evans, P
    TETRAHEDRON LETTERS, 2002, 43 (44) : 7859 - 7862
  • [28] Highly diastereoselective Pauson-Khand reactions of a stable, internally chelated, dicobalt pentacarbonyl complex of a chiral acetylene thioether
    Montenegro, E
    Poch, M
    Moyano, A
    Pericàs, MA
    Riera, A
    TETRAHEDRON LETTERS, 1998, 39 (3-4) : 335 - 338
  • [29] 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
  • [30] Heterobimetallic (Co-W) intermolecular Pauson-Khand reactions:: scope and selectivity
    Rios, R
    Pericàs, MA
    Moyano, A
    TETRAHEDRON LETTERS, 2002, 43 (28) : 4903 - 4906
12345