Diastereoselective Synthesis of Allenes through Phosphine-Catalyzed Cascade Isomerization/Annulation

被引:6
|
作者
Tang, Yi [1 ,2 ]
Shi, Wangyu [1 ,2 ]
Du, Juan [1 ,2 ]
Ren, Yue [1 ,2 ]
Xiao, Yumei [1 ,2 ]
Guo, Hongchao [1 ,2 ]
机构
[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China
[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China
基金
中国国家自然科学基金;
关键词
GAMMA-SUBSTITUTED ALLENOATES; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; CHIRAL PHOSPHINES; 3+2 ANNULATION; CYCLOADDITION; DERIVATIVES; 1,3-DIENES; CARBONATES;
D O I
10.1021/acs.orglett.3c03283
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphine-catalyzed cascade isomerization/annulation has been developed to realize a diastereoselective synthesis of allenes installed on the hexahydropentalene skeleton, which contains five chiral centers (and one axial chirality). This reaction tolerated a broad range of allenoates and enynes. The allene products were transformed to various halogen-substituted fused-ring compounds.
引用
收藏
页码:8547 / 8552
页数:6
相关论文
共 50 条
  • [1] Enantioselective Synthesis of Cyclopentanes by Phosphine-Catalyzed β,γ-Annulation of Allenoates
    Zhang, Chenxi
    Maddigan-Wyatt, Jeremy T.
    Nguyen, Xuan
    Seitz, Antonia
    Breugst, Martin
    Lupton, David W.
    ORGANIC LETTERS, 2024, 26 (37) : 7800 - 7804
  • [2] Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation
    Han, Xiaoyu
    Yao, Weijun
    Wang, Tianli
    Tan, Yong Ren
    Yan, Ziyu
    Kwiatkowski, Jacek
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5643 - 5647
  • [3] Phosphine-Catalyzed Cascade Annulation of MBH Carbonates and Diazenes: Synthesis of Hexahydrocyclopenta[c]pyrazole Derivatives
    Li, Hongxiang
    Shi, Wangyu
    Wang, Chang
    Liu, Hao
    Wang, Wei
    Wu, Yongjun
    Guo, Hongchao
    ORGANIC LETTERS, 2021, 23 (14) : 5571 - 5575
  • [4] Phosphine-catalyzed [4+2] annulation: Synthesis of cyclohexenes
    Tran, Yang S.
    Kwon, Ohyun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12632 - +
  • [5] Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Methyleneindolinone with Alkynoate Derivatives
    Zhang, Jiayong
    Cheng, Cheng
    Wang, Dian
    Miao, Zhiwei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10121 - 10128
  • [6] Highly regio- and diastereoselective construction of spirocyclopenteneoxindole phosphonates through a phosphine-catalyzed [3+2] annulation reaction
    Yu, Chengbin
    Zheng, Weiping
    Zhan, Junchen
    Sun, Yuchao
    Miao, Zhiwei
    RSC ADVANCES, 2014, 4 (108) : 63246 - 63253
  • [7] Enantioselective Synthesis of Pyrrolidines by a Phosphine-Catalyzed?-Umpolung/?-Umpolung Cascade
    Maddigan-Wyatt, Jeremy T.
    Cao, Jing
    Ametovski, Jhi
    Hooper, Joel F.
    Lupton, David W.
    ORGANIC LETTERS, 2022, 24 (15) : 2847 - 2852
  • [8] Synthesis of Dienol Ethers Using the Phosphine-Catalyzed Alkyne Isomerization Reaction
    Fu, Michael Yunyi
    Guo, Jiawen
    Toy, Patrick H.
    SYNLETT, 2011, (07) : 989 - 991
  • [9] Phosphine-Catalyzed [3+2] Annulation of Cyanoallenes
    Kinderman, Sape S.
    van Maarseveen, Jan H.
    Hiemstra, Henk
    SYNLETT, 2011, (12) : 1693 - 1696
  • [10] Phosphine-catalyzed annulation of ethyl (arylimino)acetates: synthesis of highly functionalized oxoimidazolidines
    Ma, Guang-Ning
    Wang, Fei-Jun
    Gao, Jun
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2008, (40) : 4998 - 5000