Tandem aminocarbonylation/Pauson-Khand reaction of haloacetylenes

被引:28
作者
Balsells, J [1 ]
Moyano, A [1 ]
Riera, A [1 ]
Pericàs, MA [1 ]
机构
[1] Univ Barcelona, Dept Quim Organ, Unitat Recerca Sintesi Asimetr, E-08028 Barcelona, Spain
关键词
D O I
10.1021/ol991145h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The dicobalt hexacarbonyl complex of 1-chloro-2-phenylacetylene decomposes in solution at room temperature affording similar amounts of two new complexes, to which the structures of a dichloro tetracobalt decacarbonyl complex of 1,4-diphenyl-1,3-butadiyne and of a 1-chloro-2-phenylacetylene acylcobalt complex have been tentatively assigned. The acyl complex can he efficiently trapped by amines, and the resulting aminocarbonylation products submitted to Pauson-Khand reaction to yield cyclopentenones with the regiocontrolled formation of five new bonds in a single synthetic operation.
引用
收藏
页码:1981 / 1984
页数:4
相关论文
共 22 条
  • [11] 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
    [J]. TETRAHEDRON LETTERS, 1998, 39 (3-4) : 335 - 338
  • [12] Studies on the Pauson-Khand reaction of alkynyl sulfoxides.: Unexpectedly easy racemization of their dicobalt hexacarbonyl complexes
    Montenegro, E
    Moyano, A
    Pericàs, MA
    Riera, A
    Alvarez-Larena, A
    Piniella, JF
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (03) : 457 - 471
  • [13] CHEMISTRY AND SYNTHETIC UTILITY OF COBALT-COMPLEXED PROPARGYL CATIONS
    NICHOLAS, KM
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (06) : 207 - 214
  • [14] Schore N. E., 1995, COMPREHENSIVE ORGANO, V12, P703
  • [15] N-OXIDE PROMOTED PAUSON-KHAND CYCLIZATIONS AT ROOM-TEMPERATURE
    SHAMBAYATI, S
    CROWE, WE
    SCHREIBER, SL
    [J]. TETRAHEDRON LETTERS, 1990, 31 (37) : 5289 - 5292
  • [16] Enantioselective syntheses of alpha-methylene butyrolactones via asymmetric aminocarbonylation of tungsten-prop-2-ynyl compounds
    Shiu, LH
    Wang, SL
    Wu, MJ
    Liu, RS
    [J]. CHEMICAL COMMUNICATIONS, 1997, (21) : 2055 - 2056
  • [17] Sugihara T, 1999, SYNLETT, P768
  • [18] INSERTION OF CARBON-MONOXIDE AND ALKENES IN PALLADIUM-CARBON BONDS OF COMPLEXES CONTAINING RIGID BIDENTATE NITROGEN LIGANDS - THE FIRST EXAMPLE OF ISOLATED COMPLEXES IN STEPWISE SUCCESSIVE INSERTION REACTIONS ON THE WAY TO POLYKETONES
    VANASSELT, R
    GIELENS, EECG
    RULKE, RE
    VRIEZE, K
    ELSEVIER, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) : 977 - 985
  • [19] Camphor-derived, chelating auxiliaries for the highly diastereoselective intermolecular Pauson-Khand reaction:: Experimental and computational studies
    Verdaguer, X
    Vázquez, J
    Fuster, G
    Bernardes-Génisson, V
    Greene, AE
    Moyano, A
    Pericàs, MA
    Riera, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) : 7037 - 7052
  • [20] THE DETERMINATION OF MOLECULAR-STRUCTURES BY DENSITY FUNCTIONAL THEORY - THE EVALUATION OF ANALYTICAL ENERGY GRADIENTS BY NUMERICAL-INTEGRATION
    VERSLUIS, L
    ZIEGLER, T
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1988, 88 (01) : 322 - 328