Conformational control on remote stereochemistry in the intramolecular Pauson-Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols

被引:10
|
作者
Sezer, Serdar
Ozdemirhan, Devrim
Sahin, Ertan
Tanyeli, Cihangir [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
[2] Abant Izzet Baysal Univ, Dept Chem, TR-14280 Bolu, Turkey
[3] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey
关键词
D O I
10.1016/j.tetasy.2006.11.012
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An intramolecular Pauson-Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93-99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2981 / 2986
页数:6
相关论文
共 50 条
  • [1] Intramolecular Pauson-Khand reactions of aromatic enynes
    Lovely, CJ
    Seshadri, H
    SYNTHETIC COMMUNICATIONS, 2001, 31 (16) : 2479 - 2490
  • [2] Aromatic enynes as substrates for the intramolecular Pauson-Khand reaction
    Blanco-Urgoiti, J
    Casarrubios, L
    Pérez-Castells, J
    TETRAHEDRON LETTERS, 1999, 40 (14) : 2817 - 2820
  • [3] Steric buttressing in the Pauson-Khand reactions of aryl enynes
    Madu, Christian E.
    Seshadri, Hernalatha
    Lovely, Carl J.
    TETRAHEDRON, 2007, 63 (23) : 5019 - 5029
  • [4] Steric buttressing in the Pauson-Khand reactions of benzyl enynes
    Madu, Christian E.
    Dias, H. V. Rasika
    Lovely, Carl J.
    TETRAHEDRON, 2017, 73 (43) : 6118 - 6137
  • [5] Steric promotion of the intramolecular Pauson-Khand reaction of aryl enynes
    Madu, Christian E.
    Lovely, Carl J.
    SYNLETT, 2007, (13) : 2011 - 2016
  • [6] Intramolecular Pauson-Khand reactions of cycloheptynedicobalt complexes
    Mohamed, AB
    Green, JR
    Masuda, J
    SYNLETT, 2005, (10) : 1543 - 1546
  • [7] Intermolecular and intramolecular pauson-khand reactions of functionalized allenes
    Gonzalez-Gomez, Alvaro
    Anorbe, Loreto
    Poblador, Amalia
    Dominguez, Gema
    Perez-Castells, Javier
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (08) : 1370 - 1377
  • [8] Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson-Khand reaction on camphor tethered enynes
    Sezer, Serdar
    Gumrukcu, Yasemin
    Sahin, Ertan
    Tanyeli, Cihangir
    TETRAHEDRON-ASYMMETRY, 2008, 19 (23) : 2705 - 2710
  • [9] THE VIRTUE OF METHYLENECYCLOPROPANE TERMINATORS IN INTRAMOLECULAR PAUSON-KHAND REACTIONS
    STOLLE, A
    BECKER, H
    SALAUN, J
    DEMEIJERE, A
    TETRAHEDRON LETTERS, 1994, 35 (21) : 3517 - 3520
  • [10] Intermolecular and intramolecular Pauson-Khand reactions of cyclopropenes.
    Pallerla, MK
    Fox, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U42 - U42