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
  • [21] An unexpected phosphine-catalyzed [3+2] annulation. Synthesis of highly functionalized cyclopentenes
    Lu, Zheng
    Zheng, Suqing
    Zhang, Xumu
    Lu, Xiyan
    ORGANIC LETTERS, 2008, 10 (15) : 3267 - 3270
  • [22] Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation
    Andrews, Ian P.
    Kwon, Ohyun
    CHEMICAL SCIENCE, 2012, 3 (08) : 2510 - 2514
  • [23] Phosphine-Catalyzed [4+3] Annulation for the Synthesis of Highly Functionalized Bicyclo[3.2.2]nonadienes
    Zheng, Suqing
    Lu, Xiyan
    ORGANIC LETTERS, 2009, 11 (17) : 3978 - 3981
  • [24] Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines
    Zhang, Fuhao
    Dai, Xuan
    Dai, Lei
    Zheng, Wenrui
    Chan, Wai-Lun
    Tang, Xiaodong
    Zhang, Xumu
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (24)
  • [25] An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones
    Chen, Zuliang
    Zhang, Junliang
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1542 - 1545
  • [26] Phosphine-catalyzed dearomatizing [3+2] annulations of isoquinolinium methylides with allenes
    Jia, Zhi-Jun
    Daniliuc, Constantin Gabriel
    Antonchick, Andrey P.
    Waldmann, Herbert
    CHEMICAL COMMUNICATIONS, 2015, 51 (06) : 1054 - 1057
  • [27] Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles
    Chung, Ying Kit
    Fu, Gregory C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) : 2225 - 2227
  • [28] Total Synthesis of (±)-Hirsutine: Application of Phosphine-Catalyzed Imine-Allene [4+2] Annulation
    Villa, Reymundo A.
    Xu, Qihai
    Kwon, Ohyun
    ORGANIC LETTERS, 2012, 14 (17) : 4634 - 4637
  • [29] Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isatylidene Malononitriles
    Deng, Hong-Ping
    Wei, Yin
    Shi, Min
    ORGANIC LETTERS, 2011, 13 (13) : 3348 - 3351
  • [30] Phosphine-catalyzed synthesis of highly functionalized coumarins
    Henry, Christopher E.
    Kwon, Ohyun
    ORGANIC LETTERS, 2007, 9 (16) : 3069 - 3072