Transition Metal-Catalyzed Synthesis of 1,2,3,4-Tetrasubstituted 1,3-Dienes from Propargylic Esters

被引:3
|
作者
Dai, Mengfu [1 ]
Kabandula, Lucy Felicity [1 ]
Tai, Lanzhu [1 ]
Wu, Boxue [1 ]
Song, Liangliang [2 ]
Chen, Liang-An [1 ]
机构
[1] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Sch Chem & Mat Sci, Jiangsu Key Lab New Power Batteries, Nanjing 210023, Peoples R China
[2] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
基金
中国国家自然科学基金;
关键词
Transition Metal; 1,3-Dienes; Propargylic Esters; Tetrasubstituted; Acyloxy Migration; CONTROLLED REGIODIVERGENT; ALPHA-PROPARGYLATION; CONJUGATED DIENES; ENYNE METATHESIS; CROSS-METATHESIS; EFFICIENT; ALKENES; NICKEL; ISOMERIZATIONS; REARRANGEMENT;
D O I
10.1002/cctc.202301738
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Transition metal-catalyzed synthesis of propargylic esters has been widely investigated, offering distinctive opportunities to build 1,3-diene skeletons. Access to 1,2,3,4-tetrasubstituted 1,3-dienes has been a longstanding challenge in organic synthesis due to a great diversity of stereoisomers from four substituents and unpredictable regioselectivity. Given the synthetic challenges and the importance, inventing methods for the generation of this valuable architecture has gathered much more attention. Recently, several intriguing works concerning this topic have been achieved towards the high regio- and stereoselective elaborate 1,2,3,4-tetrasubstituted 1,3-dienes. Herein, this concept summarizes recent advances in transition metal-catalyzed construction of 1,2,3,4-tetrasubstituted 1,3-dienes from propargylic esters and discusses the mechanism as well as their applications.
引用
收藏
页数:6
相关论文
共 50 条
  • [11] Synthesis of 1,2-divinylcyclopropanes by metal-catalyzed cyclopropanation of 1,3-dienes with cyclopropenes as vinyl carbene precursors
    Gonzalez, Jesus
    de la Fuente, Alba
    Gonzalez, Maria J.
    Diez de Tejada, Laura
    Lopez, Luis A.
    Vicente, Ruben
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 285 - 290
  • [12] INTERACTION OF VINYLPYRIDINES WITH 1,3-DIENES CATALYZED BY TRANSITION-METAL COMPLEXES
    SELIMOV, FA
    PTASHKO, OA
    FATYKHOV, AA
    KHALIKOVA, NR
    DZHEMILEV, UM
    RUSSIAN CHEMICAL BULLETIN, 1993, 42 (05) : 872 - 878
  • [13] REGIOSELECTIVE MONOEPOXIDATION OF 1,3-DIENES CATALYZED BY TRANSITION-METAL COMPLEXES
    THOMSEN, DS
    SCHIOTT, B
    JORGENSEN, KA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (15) : 1072 - 1074
  • [14] Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates
    Li, Guotao
    Zhang, Guozhu
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) : 3740 - +
  • [15] Facile synthesis of 1,2,3,4-tetrasubstituted pyrroles from Baylis-Hillman adducts
    Kim, Seong Jin
    Kim, Hoo Sook
    Kim, Taek Hyeon
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (09) : 1605 - 1608
  • [16] Solvent-free synthesis of 1,2,3,4-tetrasubstituted pyrroles from enaminones and β-nitrostyrenes
    Yavari, Issa
    Ghazvini, Maryam
    Aminkhani, Ali
    JOURNAL OF CHEMICAL RESEARCH, 2011, (10) : 558 - 560
  • [17] METAL COMPLEX-CATALYZED SYNTHESIS OF DIHYDROTHIAPYRANS FROM DIALKYL SULFOXIDES AND 1,3-DIENES
    DZHEMILEV, UM
    KUNAKOVA, RV
    BAIBULATOVA, NZ
    TARASENKO, AE
    MUSTAFINA, EM
    BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (01): : 128 - 134
  • [18] 1,2,3,4-TETRASUBSTITUTED ISOQUINOLINE ACETIC-ACIDS
    SCHNUR, RC
    HOWARD, HR
    TETRAHEDRON LETTERS, 1981, 22 (30) : 2843 - 2846
  • [19] Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers
    Liu, Chunxiang
    Deng, Guogang
    Li, Xin
    Xu, Yiren
    Yu, Kaili
    Chen, Wen
    Zhang, Hongbin
    Yang, Xiaodong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 483 - 487
  • [20] THERMAL REARRANGEMENTS OF PROPARGYLIC TRICHLOROACETIMIDATES - SYNTHESIS OF (TRICHLOROACETAMIDO)-1,3-DIENES AND (TRICHLOROACETAMIDO)-1,2-DIENES
    OVERMAN, LE
    CLIZBE, LA
    FREERKS, RL
    MARLOWE, CK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) : 2807 - 2815