THE [NI(CO)4]-PROMOTED CARBONYLATIVE CYCLOADDITION OF ALKYNES AND ALLYL HALIDES FOR THE SYNTHESIS OF 2-CYCLOPENTENONE DERIVATIVES

被引:18
|
作者
LLEBARIA, A [1 ]
MORETO, JM [1 ]
机构
[1] CSIC,CID,DEPT QUIM ORGAN BIOL,JORDI GIRONA 18-26,E-08034 BARCELONA,SPAIN
关键词
D O I
10.1016/0022-328X(93)83002-D
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The [Ni(CO)4]-mediated carbonylative cycloaddition of alkynes and allyl halides first reported by Chiusoli, has been reviewed, extended and optimized for application to cyclopentenone synthesis. An insight into the reaction mechanism is also given to explain the results obtained, in particular the regio- and stereo-chemistry of the process.
引用
收藏
页码:1 / 13
页数:13
相关论文
共 50 条
  • [1] INFLUENCE OF FUNCTIONAL SUBSTITUTION OF ALLYL HALIDES ON THEIR NI(CO)4 PROMOTED CARBONYLATIVE CYCLOADDITION WITH ACETYLENES
    CAMPS, F
    MORETO, JM
    PAGES, L
    TETRAHEDRON, 1992, 48 (15) : 3147 - 3162
  • [2] Carbonylative cycloaddition of allyl halides and acetylenes promoted by Ni(CO)4.: A DFT study on the reaction mechanism
    Carbó, JJ
    Bo, C
    Poblet, JM
    Moretó, JM
    ORGANOMETALLICS, 2000, 19 (18) : 3516 - 3526
  • [3] Synthesis of New Pyrazoles via Cycloaddition Reactions of Nitrilimines with 2-Cyclopentenone Derivatives
    El-Samahy, Fatma A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (02) : 597 - 602
  • [4] STUDIES FOR CONTROL OF THE NI(CO)4-PROMOTED CARBONYLATIVE CYCLO-ADDITION OF ALLYL HALIDES AND ACETYLENES
    CAMPS, F
    COLL, J
    MORETO, JM
    TORRAS, J
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08): : 1969 - 1978
  • [5] Preference for β-H elimination in the termination of the Ni-promoted carbonylative cycloaddition of 2-haloethylidene-cycloalkanes and alkynes
    Vilaseca, F
    Pages, L
    Villar, JM
    Llebaria, A
    Delgado, A
    Moreto, JM
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 551 (1-2) : 107 - 115
  • [6] Palladium-catalyzed synthesis of β-lactams via carbonylative cycloaddition of benzyl and allyl halides with imines
    Cho, CS
    Jiang, LH
    Shim, SC
    SYNTHETIC COMMUNICATIONS, 1999, 29 (15) : 2695 - 2703
  • [7] Stereoselective synthesis of polyfunctionalised hydroxylated cyclopentanes from dihydroxylated 2-cyclopentenone derivatives
    Caddick, S
    Cheung, S
    Doyle, VE
    Frost, LM
    Soscia, MG
    Delisser, VM
    Williams, MRV
    Etheridge, ZC
    Khan, S
    Hitchcock, PB
    Pairaudeau, G
    Vile, S
    TETRAHEDRON, 2001, 57 (29) : 6295 - 6303
  • [8] New Fischer carbene complexes of rhodium(I):: Preparation and 2-cyclopentenone ring synthesis by annelation to alkynes
    Barluenga, J
    Vicente, R
    López, LA
    Rubio, E
    Tomás, M
    Alvarez-Rúa, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) : 470 - 471
  • [9] A 2 STEP PROCEDURE AS IMPROVED ALTERNATIVE TO THE CYCLOCARBONYLATION OF ALLYL HALIDES AND ACETYLENE DERIVATIVES MEDIATED BY NI(CO)4
    CAMPS, F
    COLL, J
    LLEBARIA, A
    MORETO, JM
    TETRAHEDRON LETTERS, 1988, 29 (45) : 5811 - 5814
  • [10] Synthesis of 2-Cyclopentenone Derivatives via Palladium-Catalyzed Intramolecular Carbonyl α-Alkenylation
    Chen, Panpan
    Meng, Yinggao
    Wang, Han
    Han, Feipeng
    Wang, Yulong
    Song, Chuanjun
    Chang, Junbiao
    ORGANIC LETTERS, 2016, 18 (15) : 3914 - 3917