Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions

被引:384
作者
Lloyd-Jones, GC [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
关键词
D O I
10.1039/b209175p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isotopic, kinetic, spectroscopic, structural and computational investigations into the mechanism by which transition metals effect cycloisomerization are reviewed. Focus is on 1,6-diene and 1,6-enyne transition metal catalyzed cycloisomerization reactions. It is emphasized that all aspects of cycloisomerization would benefit from increased mechanistic insight and in the long term this will be the key to increasing catalyst efficiency, inducing or improving regio- chemo- or enantio-selectivities or eliminating cycloisomerization as side reaction.
引用
收藏
页码:215 / 236
页数:22
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共 142 条
  • [81] Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes
    Mori, M
    Sakakibara, N
    Kinoshita, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) : 6082 - 6083
  • [82] Intramolecular cyclizations of enynes using RuClH(CO)(PPh3)3
    Nishida, M
    Adachi, N
    Onozuka, K
    Matsumura, H
    Mori, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9158 - 9159
  • [83] Cationic platinum-complex-catalyzed skeletal reorganization of enynes
    Oi, S
    Tsukamoto, I
    Miyano, S
    Inoue, Y
    [J]. ORGANOMETALLICS, 2001, 20 (17) : 3704 - 3709
  • [84] Transition metal-catalyzed carbocyclizations in organic synthesis
    Ojima, I
    Tzamarioudaki, M
    Li, ZY
    Donovan, RJ
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 635 - 662
  • [85] Titanium(IV) aryloxide catalyzed cyclization reactions of 1,6-and 1,7-dienes
    Okamoto, S
    Livinghouse, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) : 1223 - 1224
  • [86] Titanium-catalyzed cycloisomerization of 1,6-dienes.: Regio- and stereoselective synthesis of exo-methylenecycloalkanes
    Okamoto, S
    Livinghouse, T
    [J]. ORGANOMETALLICS, 2000, 19 (08) : 1449 - 1451
  • [87] Direct observation of the conversion of a palladium 5-hexenyl chelate complex to a palladium cyclopentylmethyl complex
    Perch, NS
    Widenhoefer, RA
    [J]. ORGANOMETALLICS, 2001, 20 (25) : 5251 - 5253
  • [88] Room temperature operating allenylidene precatalyst [LnRu=C=C=CR2](+)X- for olefin metathesis:: dramatic influence of the counter anion X-
    Picquet, M
    Touchard, D
    Bruneau, C
    Dixneuf, PH
    [J]. NEW JOURNAL OF CHEMISTRY, 1999, 23 (02) : 141 - 143
  • [89] PIERS WE, 1990, SYNLETT, P74
  • [90] Carbohydrate carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis
    Poulsen, CS
    Madsen, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) : 4441 - 4449