Metal-catalyzed regioselective oxy-functionalization of internal alkynes: An entry into ketones, acetals, and spiroketals

被引:209
作者
Liu, Bo [1 ]
De Brabander, Jef K. [1 ]
机构
[1] Univ Texas, SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA
关键词
D O I
10.1021/ol0619819
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Platinum(II) and an unusual cationic gold( I) complex were identified as mild catalysts for the room temperature cycloisomerization or tandem hydroalkoxylation/acetal formation of unactivated internal alkynols. Under the appropriate conditions, 5-endo, 5-exo, 6-endo, and 6-exo cycloisomerization modes are all available.
引用
收藏
页码:4907 / 4910
页数:4
相关论文
共 26 条
  • [1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [2] Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols
    Antoniotti, S
    Genin, E
    Michelet, V
    Genêt, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9976 - 9977
  • [3] Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions
    Barluenga, J
    Diéguez, A
    Fernández, A
    Rodríguez, F
    Fañanás, FJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) : 2091 - 2093
  • [4] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    Beller, M
    Seayad, J
    Tillack, A
    Jiao, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
  • [5] Cyclisation of acetylenic carboxylic acids and acetylenic alcohols to oxygen-containing heterocycles using cationic rhodium(I) complexes
    Elgafi, S
    Field, LD
    Messerle, BA
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) : 97 - 104
  • [6] EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST
    FUKUDA, Y
    UTIMOTO, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) : 3729 - 3731
  • [7] An IrI-catalyzed exo-selective tandem cycloisomerization/hydroalkoxylation of bis-homopropargylic alcohols at room temperature
    Genin, E
    Antoniotti, S
    Michelet, V
    Genet, JP
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) : 4949 - 4953
  • [8] Platinum(II)-catalyzed addition of alcohols to alkynes
    Hartman, JW
    Sperry, L
    [J]. TETRAHEDRON LETTERS, 2004, 45 (19) : 3787 - 3788
  • [9] Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO
  • [10] 2-F