Palladium-Catalyzed [5+4] Cycloaddition of 4-Vinyl-4-Butyrolactones with N-Tosyl Azadienes: Construction of Nine-Membered Ring

被引：5
|
作者：
Wang, Lan [1 ]
Yang, Sen [1 ]
Tang, Yi [1 ]
Li, Kuan [1 ]
Lu, Mengxi [1 ]
Guo, Hongchao [1 ]
机构：
[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 07期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE SYNTHESIS; VINYLETHYLENE CARBONATES; BENZOFURAN DERIVATIVES; HETEROCYCLES; ANNULATION; ACCESS; REARRANGEMENT; IMINES;
D O I：
10.1021/acs.joc.4c00245
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper, we reported the palladium-catalyzed formal [5 + 4] cycloaddition reactions between 4-vinyl-4-butyrolactones (VBLs) and azadienes. Under mild reaction conditions, a wide range of benzofuran-fused 9-membered heterocyclic compounds had been provided in moderate to excellent yields with exclusive regioselectivities and excellent diastereoselectivities. The practical applicability of the synthesis was demonstrated through scale-up reaction and further transformation.
引用
收藏
页码：5019 / 5028
页数：10
相关论文
共 50 条
  • [1] Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition
    Yang, Li-Cheng
    Rong, Zi-Qiang
    Wang, Ya-Nong
    Tan, Zher Yin
    Wang, Min
    Zhao, Yu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (11) : 2927 - 2931
  • [2] Palladium-Catalyzed (5+3) Annulation of 4-Vinyl-4-Butyrolactones with C,N-Cyclic Azomethine Imines: Construction of Eight-Membered Ring
    Yang, Sen
    Li, Kuan
    Tang, Yi
    Zheng, Bing
    Wang, Wei
    Wu, Yongjun
    Xiao, Yumei
    Guo, Hongchao
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) : 3967 - 3972
  • [3] Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-Butyrolactones with Alkenes: Synthesis of Spirocyclopentane Compounds
    Sun, Honghao
    Song, Aoran
    Gu, Shuang
    Tang, Yi
    Yang, Sen
    Li, Wenhui
    Guo, Hongchao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (19): : 14141 - 14150
  • [4] Palladium-catalyzed [3+2] cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines: construction of sulfamate-fused pyrrolidines
    Sun, Honghao
    Ding, Siyuan
    Wang, Bo
    Huang, Jiaxing
    Guo, Hongchao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 23 (01) : 90 - 93
  • [5] Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-butyrolactones with Ketenes Generated in Situ from Acyl Chlorides: A Method for the Synthesis of Dihydrofurans
    Dong, Yujie
    Yang, Sen
    Tang, Yi
    Li, Kuan
    Liu, Jun
    Yang, Fazhou
    Zhang, Cheng
    Guo, Hongchao
    ORGANIC LETTERS, 2024, 26 (10) : 2057 - 2061
  • [6] Construction of eight-membered carbocycles by palladium-catalyzed [4+4] cycloaddition of vinylallenes
    Murakami, M
    Itami, K
    Ito, Y
    SYNLETT, 1999, : 951 - 953
  • [7] Single-step construction of a nine-membered carbocycle by a new [4+4+1] cycloaddition
    Murakami, M
    Itami, K
    Ito, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (24) : 3418 - 3420
  • [8] Palladium-Catalyzed Carbonylative [5+1] Cycloaddition of N-Tosyl Vinylaziridines: Solvent-Controlled Divergent Synthesis of α,β- and β,γ-Unsaturated δ-Lactams
    Zhang, Tao
    Wang, Shichong
    Zuo, Dandan
    Zhao, Jingjing
    Luo, Wen
    Wang, Chaojie
    Li, Pan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10408 - 10415
  • [9] Catalyst-Controlled Switchable (5+4)/(3+4) Cycloadditions for the Divergent Synthesis of Pyrazole-Fused Seven- and Nine-Membered Heterocycles
    Wang, Jie
    Qi, Ting
    He, Shurong
    Huang, Wei
    Peng, Cheng
    Zhan, Gu
    Han, Bo
    ACS CATALYSIS, 2023, 13 (16) : 10694 - 10704
  • [10] Palladium-catalyzed enantioselective [5+4] annulation ofortho-quinone methides and vinylethylene carbonates
    Xia, Chao
    Wang, Dong-Chao
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (12): : 1474 - 1480
12345