Enantioselective ruthenium-catalyzed ring-closing metathesis

被引:405
作者
Seiders, TJ [1 ]
Ward, DW [1 ]
Grubbs, RH [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Lab Chem Synth, Pasadena, CA 91125 USA
关键词
D O I
10.1021/ol0165692
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS The first enantioselective ruthenium olefin metathesis catalysts have been prepared, and high enantiomeric excesses (up to 90%) are observed in the desymmetrization of achiral trienes. A model consistent with the stereochemical outcome of the reactions is described and suggests side-on olefin binding and reorganization of the halide ligands.
引用
收藏
页码:3225 / 3228
页数:4
相关论文
共 53 条
  • [1] Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry
    Adlhart, C
    Hinderling, C
    Baumann, H
    Chen, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8204 - 8214
  • [2] Aeilts SL, 2001, ANGEW CHEM INT EDIT, V40, P1452, DOI 10.1002/1521-3773(20010417)40:8<1452::AID-ANIE1452>3.0.CO
  • [3] 2-G
  • [4] Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex
    Alexander, JB
    La, DS
    Cefalo, DR
    Hoveyda, AH
    Schrock, RR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4041 - 4042
  • [5] Cyclopropanation of styrene with ethyl diazoacetate catalyzed by chiral and achiral ruthenium 2,6-bis(imino)pyridyl complexes
    Bianchini, C
    Lee, HM
    [J]. ORGANOMETALLICS, 2000, 19 (10) : 1833 - 1840
  • [6] Bielawski CW, 2000, ANGEW CHEM INT EDIT, V39, P2903, DOI 10.1002/1521-3773(20000818)39:16<2903::AID-ANIE2903>3.0.CO
  • [7] 2-Q
  • [8] STRUCTURE OF BIS(DIMETHYLPHENYLPHOSPHINE)(ETHYLENE)(CARBONYL) DICHLORORUTHENIUM(II), RUCL2(CO)(C2H4)(P(CH3)2(C6H5))2, A 6-COORDINATE D6 COMPLEX CONTAINING ETHYLENE AS A LIGAND
    BROWN, LD
    BARNARD, CFJ
    DANIELS, JA
    MAWBY, RJ
    IBERS, JA
    [J]. INORGANIC CHEMISTRY, 1978, 17 (10) : 2932 - 2935
  • [9] Enantioselective synthesis of unsaturated cyclic tertiary ethers by Mo-catalyzed olefin metathesis
    Cefalo, DR
    Kiely, AF
    Wuchrer, M
    Jamieson, JY
    Schrock, RR
    Hoveyda, AH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) : 3139 - 3140
  • [10] Synthesis of functionalized olefins by cross and ring-closing metatheses
    Chatterjee, AK
    Morgan, JP
    Scholl, M
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) : 3783 - 3784