Chiral cyclopentadiene-mediated approach to enantio selective heterobimetallic Pauson-Khand reactions

被引：18
|
作者：
Rios, R [1 ]
Paredes, S [1 ]
Pericàs, MA [1 ]
Moyano, A [1 ]
机构：
[1] Univ Barcelona, Fac Quim, Dept Quim Organ, Unitat Recerca Sintesi Asimetr, E-08028 Barcelona, Spain
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2005年 / 690卷 / 02期
关键词：
alkynes; asymmetric synthesis; chiral cyclopentadienes; cobalt; molybdenum; Pauson-Khand reactions;
D O I：
10.1016/j.jorganchem.2004.09.046
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
When the dicobalt(hexacarbonyl) complex of N-(2-butynoyl)-4,4-dimethyloxazolidinone (1) is treated with chiral cyclopentadienyl (tricarbonyl)molybdenum anions, pairs of diastereomeric heterobimetallic (Co-Mo) complexes are obtained. In one instance, the two diastereomers have been separated by chromatography and they have been reacted with norbornadiene; each diastereomer leads with virtually complete stereocontrol to a single enantionter of the endo Pauson-Khand cycloadduct 5. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码：358 / 362
页数：5
相关论文
共 50 条
  • [1] Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes
    Pallerla, MK
    Fox, JM
    ORGANIC LETTERS, 2005, 7 (16) : 3593 - 3595
  • [2] ENANTIOSELECTIVE PAUSON-KHAND REACTIONS MEDIATED BY A CHIRAL AMINE N-OXIDE
    KERR, WJ
    KIRK, GG
    MIDDLEMISS, D
    SYNLETT, 1995, (10) : 1085 - &
  • [3] An intramolecular Pauson-Khand approach to the synthesis of chiral cyclopentadienes
    Rios, R
    Moyano, A
    Pericàs, MA
    TETRAHEDRON LETTERS, 2002, 43 (06) : 1023 - 1026
  • [4] Pauson-Khand reactions in water
    Krafft, ME
    Wright, JA
    Boñaga, L
    CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (6-7) : 1006 - 1016
  • [5] ENANTIOSELECTIVE PAUSON-KHAND REACTIONS
    CASTRO, J
    GREENE, AE
    MOYANO, A
    PERICAS, MA
    POCH, M
    RIERA, A
    SOLA, L
    VERDAGUER, X
    ANALES DE QUIMICA, 1993, 89 (01): : 135 - 136
  • [6] Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions.
    Montenegro, E
    Poch, M
    Moyano, A
    Pericas, MA
    Riera, A
    TETRAHEDRON, 1997, 53 (25) : 8651 - 8664
  • [7] A pauson-khand approach to the hamigerans
    Madu, Christian E.
    Lovely, Carl J.
    ORGANIC LETTERS, 2007, 9 (23) : 4697 - 4700
  • [8] Heterobimetallic (Co-W) intermolecular Pauson-Khand reactions:: scope and selectivity
    Rios, R
    Pericàs, MA
    Moyano, A
    TETRAHEDRON LETTERS, 2002, 43 (28) : 4903 - 4906
  • [9] 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
  • [10] Microwave promoted Pauson-Khand reactions
    Iqbal, M
    Vyse, N
    Dauvergne, J
    Evans, P
    TETRAHEDRON LETTERS, 2002, 43 (44) : 7859 - 7862
12345