A novel titanium tetrahalide-mediated carbon-carbon bond-forming reaction:: Regioselective synthesis of substituted (E,Z)-1,5-dihalo-1,4-dienes

被引：36
作者：
Kabalka, GW [1 ]
Wu, ZZ
Ju, YH
机构：
[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
[2] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 20期
关键词：
D O I：
10.1021/ol026507r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Reactions of aldehydes with 2 equiv of alkyne in the presence of TiX4 (X = Cl, Br) regioselectively generated 1,5-dihalo-1,4-dienes in moderate to good yields with high (E,Z)-stereoselectivity.
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收藏
页码：3415 / 3417
页数：3
相关论文
共 52 条
  • [11] Enolate formation from cyclopropyl ketones via iodide-induced ring opening and its use for stereoselective aldol reaction
    Han, Z
    Uehira, S
    Tsuritani, T
    Shinokubo, H
    Oshima, K
    [J]. TETRAHEDRON, 2001, 57 (06) : 987 - 995
  • [12] Han ZF, 2001, SYNLETT, P1421
  • [13] TRANSIENT TITANIUM ENOLATE ALDOL CONDENSATIONS
    HARRISON, CR
    [J]. TETRAHEDRON LETTERS, 1987, 28 (36) : 4135 - 4138
  • [14] HARUTA J, 1989, CHEM COMMUN, P1065
  • [15] ISHIBASHI H, 1991, CHEM PHARM BULL, V39, P1148
  • [16] A new reaction of aryl aldehydes with aryl acetylenes in the presence of boron trihalides
    Kabalka, GW
    Wu, ZZ
    Ju, YH
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1491 - 1493
  • [17] Kataoka T, 2000, ANGEW CHEM INT EDIT, V39, P2358, DOI 10.1002/1521-3773(20000703)39:13<2358::AID-ANIE2358>3.0.CO
  • [18] 2-Y
  • [19] Carbocyclization reaction of active methine compounds with unactivated alkenyl or alkynyl groups mediated by TiCl4-Et3N
    Kitagawa, O
    Suzuki, T
    Inoue, T
    Watanabe, Y
    Taguchi, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9470 - 9475
  • [20] Alkylation of carbonyl compounds in the TiCl4-promoted reaction of trimethylsilyl enol ethers with epoxides
    Lalic, G
    Petrovski, Z
    Galonic, D
    Matovic, R
    Saicic, RN
    [J]. TETRAHEDRON, 2001, 57 (03) : 583 - 591
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