Amine N-oxides derived from alkaloids as chiral promoters in enantioselective Pauson-Khand reactions

被引：0
|
作者：
Derdau, V
Laschat, S
Jones, PG
机构：
[1] Tech Univ Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
[2] Tech Univ Braunschweig, Inst Anorgan & Analyt Chem, D-38106 Braunschweig, Germany
来源：
HETEROCYCLES | 1998年 / 48卷 / 07期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The novel indolizino[3,4-b]quinoline N-oxide (12) was prepared and characterized by X-Ray crystal structure determination. Compound (12) and sparteine N-oxides (8-10) were employed as chiral promoters in the Pauson-Khand cocyclization of various alkynes (1) with norbornene (4) to the bicyclic cyclopentenones (6) with enantioselectivities up to 33 %ee.
引用
收藏
页码：1445 / 1453
页数：9
相关论文
共 50 条
  • [31] Totally stereocontrolled intermolecular Pauson-Khand reactions of N-(2-alkynoyl) sultams
    J Am Chem Soc, 42 (10225):
  • [32] Enantioselective Strecker reaction promoted by chiral N-oxides
    Liu, B
    Feng, XM
    Chen, FX
    Zhang, GL
    Cui, X
    Jiang, YZ
    SYNLETT, 2001, (10) : 1551 - 1554
  • [33] Low-energy pathway for Pauson-Khand reactions:: Synthesis and reactivity of dicobalt hexacarbonyl complexes of chiral ynamines
    Balsells, J
    Vázquez, J
    Moyano, A
    Pericàs, MA
    Riera, A
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22): : 7291 - 7302
  • [34] 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
  • [35] Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane
    Chelucci, Giorgio
    Baldino, Salvatore
    Pinna, Gerard A.
    Benaglia, Maurizio
    Buffa, Laura
    Guizzetti, Stefania
    TETRAHEDRON, 2008, 64 (32) : 7574 - 7582
  • [36] Diversity oriented synthesis of tricyclic compounds from glycals using the Ferrier and the Pauson-Khand reactions
    Hotha, S
    Tripathi, A
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (06): : 968 - 976
  • [37] Stereoselective inter- and intramolecular Pauson-Khand reactions of N-(2-alkynoyl) derivatives of chiral oxazolidin-2-ones
    Fonquerna, S
    Rios, R
    Moyano, A
    Pericàs, MA
    Riera, A
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (12) : 3459 - 3478
  • [38] OXYGEN TRANSFER REACTIONS OF AROMATIC AMINE N-OXIDES
    KOENIG, T
    TETRAHEDRON LETTERS, 1965, (35) : 3127 - &
  • [39] STEREOSELECTIVE PAUSON-KHAND REACTIONS VIA THE CHIRAL [(ALKYNE)CO-2(CO)(5)(P(OME)(3))]
    PARK, HJ
    LEE, BY
    KANG, YK
    CHUNG, YK
    ORGANOMETALLICS, 1995, 14 (06) : 3104 - 3107
  • [40] Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by chiral N,N′-dioxides and monodentate N-oxides
    Nakajima, M
    Yokota, T
    Saito, M
    Hashimoto, S
    TETRAHEDRON LETTERS, 2004, 45 (01) : 61 - 64
12345