Regio- and stereoselective hydrohalogenation of ynamide components in 1,3-butadiynes with in situ generated HX

被引:14
|
作者
Ide, Masataka [1 ]
Ohashi, Kazuhiro [1 ]
Mihara, Shigenori [1 ]
Iwasawa, Tetsuo [1 ]
机构
[1] Ryukoku Univ Otsu, Fac Sci & Technol, Dept Mat Chem, Shiga 5202194, Japan
关键词
Haloenamide; Diene; Hydrohalogenation; Regio- and stereoselective reaction; Enyne; COENZYME-A REDUCTASE; VINYL HALIDES; ALKYNES; ALKENES; ML-236B; I-2; IODOTRIMETHYLSILANE; STEREOCHEMISTRY; HYDROIODINATION; PATHWAYS;
D O I
10.1016/j.tetlet.2014.02.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple protocol for regio-, and stereoselective hydrohalogenation of ynamide moieties in 1,3-butadiyne structures is described. The facile approach enables exact syn-addition of HX to the diyne components, giving just single isomer of the corresponding dienes and enynes. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2130 / 2133
页数:4
相关论文
共 50 条
  • [21] Regio- And stereoselective cobalt-catalyzed hydrosilylation of 1,3-diynes with primary and secondary silanes
    Shen, Shaocong
    Zong, Zhijian
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    Hu, Xinquan
    Jin, Liqun
    Organic Chemistry Frontiers, 2021, 8 (22) : 6317 - 6322
  • [22] Regio- and stereoselective cobalt-catalyzed hydrosilylation of 1,3-diynes with primary and secondary silanes
    Shen, Shaocong
    Zong, Zhijian
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    Hu, Xinquan
    Jin, Liqun
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22): : 6317 - 6322
  • [23] Regio- and Stereoselective Intermolecular Oxysulfonylation of Alkynes with 1,3-Diketones to Access (Z)-β-Sulfonated Enethers
    Bhadoria, Deepak
    Kumar, Rajesh
    Kant, Ruchir
    Kumar, Atul
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13666 - 13677
  • [24] Bis(phosphine)cobalt-Catalyzed Highly Regio- and Stereoselective Hydrosilylation of 1,3-Diynes
    Kong, Degong
    Hu, Bowen
    Yang, Min
    Gong, Dawei
    Xia, Haiping
    Chen, Dafa
    ORGANOMETALLICS, 2020, 39 (24) : 4437 - 4443
  • [25] Novel and highly regio- and stereoselective nickel-catalyzed homoallylation of benzaldehyde with 1,3-dienes
    Kimura, M
    Ezoe, A
    Shibata, K
    Tamaru, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4033 - 4034
  • [26] Highly Regio- and Stereoselective Tridentate NCNN Cobalt-Catalyzed 1,3-Diyne Hydrosilylation
    Kong, Degong
    Hu, Bowen
    Yang, Min
    Chen, Dafa
    Xia, Haiping
    ORGANOMETALLICS, 2019, 38 (21) : 4341 - 4350
  • [27] 1,3-dipolar cycloaddition of 3-arylidenechromanone-1-thiochromanone and -flavanone: Regio- and stereoselective formation of spiroheterocycles
    Fisera, L
    Jaroskova, L
    Levai, A
    Jedlovska, E
    Toth, G
    Polakova, M
    HETEROCYCLES, 1997, 45 (09) : 1651 - 1655
  • [28] Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes
    Burgio, Ariel L.
    Buchbinder, Nicklas W.
    Santos, Webster L.
    ORGANIC LETTERS, 2023, 25 (15) : 2652 - 2656
  • [29] Chemo-, regio- and stereoselective addition of nitrile oxides to cobalt-coordinated 1,3-enynes
    Dare, S
    Ducroix, B
    Bernard, S
    Nicholas, KM
    TETRAHEDRON LETTERS, 1996, 37 (25) : 4341 - 4344
  • [30] A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation
    Prasanna, Pitchaimani
    Balamurugan, Kamaraj
    Perumal, Subbu
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 5653 - 5661