Copper-Catalyzed Cycloisomerizations of Enynols and Their Esters

被引:26
作者
Fehr, Charles [1 ]
机构
[1] Firmenich Co, Corp R&D Div, CH-1211 Geneva 8, Switzerland
关键词
copper catalysis; cycloisomerizations; fragrances; alkynes; gold catalysis; HOMOGENEOUS GOLD CATALYSIS; FACE-SELECTIVE PLATINUM; ENT-BETA-SANTALENE; PTCL2-MEDIATED CYCLOISOMERIZATION; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; PROPARGYLIC ESTERS; MECHANISTIC INSIGHTS; EFFICIENT SYNTHESIS; CHIRALITY TRANSFER;
D O I
10.1055/s-0031-1290657
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have discovered that several platinum-or gold-catalyzed cycloisomerization reactions can also be catalyzed by copper. This Account discusses our new findings, the complementarity of copper-catalysis, and its application to the synthesis of (-)-cubebol, (-)-beta-santalol, and other fragrance compounds.
引用
收藏
页码:990 / 1006
页数:17
相关论文
共 73 条
  • [1] Exploiting [2+2] cycloaddition chemistry: achievements with allenes
    Alcaide, Benito
    Almendros, Pedro
    Aragoncillo, Cristina
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 783 - 816
  • [2] PtCl2-mediated cycloisomerization of unsaturated propargylic carboxylates
    Anjum, S
    Marco-Contelles, J
    [J]. TETRAHEDRON, 2005, 61 (20) : 4793 - 4803
  • [3] Rearrangement of propargylic esters:: Metal-based stereospecific synthesis of (E)- and (Z)-Knoevenagel derivatives
    Barluenga, Jose
    Riesgo, Lorena
    Vicente, Ruben
    Lopez, Luis A.
    Tomas, Miguel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) : 7772 - +
  • [4] Baumann M., 1980, [No title captured], Patent No. [EP 0010213, 0010213]
  • [5] PtCl2-catalyzed transannular cycloisomerization of 1,5-enynes:: A new efficient regio- and stereocontrolled access to tricyclic derivatives
    Blaszykowski, C
    Harrak, Y
    Gonçalves, MH
    Cloarec, JM
    Dhimane, AL
    Fensterbank, L
    Malacria, M
    [J]. ORGANIC LETTERS, 2004, 6 (21) : 3771 - 3774
  • [6] Platinum(II) chloride catalyzed cycloisomerizations of 1,5-enynes
    Blaszykowski, Christophe
    Harrak, Youssef
    Brancour, Celia
    Nakama, Kimitaka
    Dhimane, Anne-Lise
    Fensterbank, Louis
    Malacria, Max
    [J]. SYNTHESIS-STUTTGART, 2007, 13 (13): : 2037 - 2049
  • [7] SILVER MEDIATED ACETYLENIC OXY COPE REARRANGEMENT
    BLUTHE, N
    GORE, J
    MALACRIA, M
    [J]. TETRAHEDRON, 1986, 42 (05) : 1333 - 1344
  • [8] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones
    Buzas, Andrea
    Gagosz, Fabien
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12614 - 12615
  • [10] Reactivity and selectivity of 1,3-diyn-6-enes in electrophilic transition metal-catalyzed reactions
    Cho, Eun Jin
    Kim, Mansuk
    Lee, Daesung
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5413 - 5416