Kinetically controlled cross-metathesis reactions with high E-olefin selectivities

被引:53
作者
Engelhardt, FC [1 ]
Schmitt, MJ [1 ]
Taylor, RE [1 ]
机构
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
关键词
D O I
10.1021/ol016061z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Homoallylic alcohols with anti-allylic substituents display enhanced E-olefin selectivity in cross-metathesis (CM) reactions with allyltrimethylsilane. The high selectivity can be explained via a five membered chelate intermediate in which the hydroxyl group of the homoallylic alcohol coordinates to the ruthenium metal center of Grubbs' catalyst.
引用
收藏
页码:2209 / 2212
页数:4
相关论文
共 21 条
  • [1] New approaches to olefin cross-metathesis
    Blackwell, HE
    O'Leary, DJ
    Chatterjee, AK
    Washenfelder, RA
    Bussmann, DA
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) : 58 - 71
  • [2] Synthesis of trisubstituted alkenes via olefin cross-metathesis
    Chatterjee, AK
    Grubbs, RH
    [J]. ORGANIC LETTERS, 1999, 1 (11) : 1751 - 1753
  • [3] Choi TL, 2001, ANGEW CHEM INT EDIT, V40, P1277, DOI 10.1002/1521-3773(20010401)40:7<1277::AID-ANIE1277>3.3.CO
  • [4] 2-5
  • [5] Preparation of allylsilanes via cross-metathesis
    Crowe, WE
    Goldberg, DR
    Zhang, ZJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (13) : 2117 - 2120
  • [6] Well-defined ruthenium olefin metathesis catalysts: Mechanism and activity
    Dias, EL
    Nguyen, ST
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) : 3887 - 3897
  • [7] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
  • [8] Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations
    Furstner, A
    Langemann, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) : 9130 - 9136
  • [9] Exploiting the reversibility of olefin metathesis.: Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin
    Fürstner, A
    Thiel, OR
    Ackermann, L
    [J]. ORGANIC LETTERS, 2001, 3 (03) : 449 - 451
  • [10] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts
    Garber, SB
    Kingsbury, JS
    Gray, BL
    Hoveyda, AH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8168 - 8179