Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic [nm0] rings

被引:175
作者
Kim, SH [1 ]
Zuercher, WJ [1 ]
Bowden, NB [1 ]
Grubbs, RH [1 ]
机构
[1] CALTECH,ARNOLD & MABEL BECKMAN LABS CHEM SYNTHESIS,DIV CHEM & CHEM ENGN,PASADENA,CA 91125
关键词
D O I
10.1021/jo951648a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium carbene 1 (Cl-2(PCy(3))(2)Ru=CHCH=CPh(2)) mediates the efficient and selective conversion of acyclic dienynes to fused bicyclic [n.m.O] rings containing five-, six-, and seven-membered rings. Studies with various X-substituted acetylenes (X=H, alkyls, Ph, CO(2)Me, SnBu(3), TMS, Cl, Pr, I) suggest that the dienyne metathesis is sensitive not only to these substituents but also to the catalysts employed. Among the various metal alkylidenes examined, only the ruthenium catalyst 1 exhibited metathesis activity for a range of substrates. These observations further expand the scope of catalytic RCM for the construction of complex organic compounds.
引用
收藏
页码:1073 / 1081
页数:9
相关论文
共 31 条
  • [1] LIVING RING-OPENING METATHESIS POLYMERIZATION OF 2,3-DIFUNCTIONALIZED 7-OXANORBORNENES AND 7-OXANORBORNADIENES BY MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(O-TERT-BU)2 AND MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(OCME2CF3)2
    BAZAN, GC
    OSKAM, JH
    CHO, HN
    PARK, LY
    SCHROCK, RR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) : 6899 - 6907
  • [2] THE FIRST SYNTHESIS OF THE ABCD RING-SYSTEM OF MANZAMINE-A - CONSTRUCTION OF THE MACROCYCLIC RING-D
    BORER, BC
    DEERENBERG, S
    BIERAUGEL, H
    PANDIT, UK
    [J]. TETRAHEDRON LETTERS, 1994, 35 (19) : 3191 - 3194
  • [3] A CYCLOMETALATED ARYLOXY(CHLORO)NEOPENTYLIDENETUNGSTEN COMPLEX - A HIGHLY-ACTIVE AND STEREOSELECTIVE CATALYST FOR THE METATHESIS OF CIS-2-PENTENE, AND TRANS-2-PENTENE, NORBORNENE, 1-METHYL-NORBORNENE, AND ETHYL OLEATE
    COUTURIER, JL
    PAILLET, C
    LECONTE, M
    BASSET, JM
    WEISS, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (05): : 628 - 631
  • [4] DIAS EW, UNPUB
  • [5] SYNTHESIS OF CYCLOALKENES VIA ALKYLIDENE-MEDIATED OLEFIN METATHESIS AND CARBONYL OLEFINATION
    FU, GC
    GRUBBS, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3800 - 3801
  • [6] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX
    FU, GC
    NGUYEN, ST
    GRUBBS, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) : 9856 - 9857
  • [7] SYNTHESIS OF NITROGEN-HETEROCYCLES VIA CATALYTIC RING-CLOSING METATHESIS OF DIENES
    FU, GC
    GRUBBS, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) : 7324 - 7325
  • [8] THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES
    FU, GC
    GRUBBS, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5426 - 5427
  • [9] THE SYNTHESIS OF CYCLIC ENOL ETHERS VIA MOLYBDENUM ALKYLIDENE-CATALYZED RING-CLOSING METATHESIS
    FUJIMURA, O
    FU, GC
    GRUBBS, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4029 - 4031
  • [10] Grubbs R. H., 1991, COMPREHENSIVE ORGANI, V5