Asymmetric Construction of Highly Functionalized Spirobarbiturate-Cyclopentenes through Chiral Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Barbiturate-Derived Alkenes

被引:52
|
作者
Liu, Yang [1 ]
Yang, Wenjun [1 ]
Wu, Yang [1 ]
Mao, Biming [1 ]
Gao, Xing [1 ]
Liu, Honglei [1 ]
Sun, Zhanhu [1 ]
Xiao, Yumei [1 ]
Guo, Hongchao [1 ]
机构
[1] China Agr Univ, Dept Appl Chem, 2 West Yuanmingyuan Rd, Beijing 100193, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
alkenes; allenoates; annulation; phosphines; spirobarbiturates; ENANTIOSELECTIVE TOTAL-SYNTHESIS; C; N-CYCLIC AZOMETHINE IMINES; ELECTRON-DEFICIENT ALKENES; DIPEPTIDE-BASED PHOSPHINES; CYCLOADDITION REACTIONS; ACTIVATED OLEFINS; ACID; DERIVATIVES; ALLENOATES; ALLENES;
D O I
10.1002/adsc.201600450
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A multifunctional chiral phosphine-catalyzed enantioselective [3+2] annulation of Morita-Baylis-Hillman carbonates with barbiturate-derived alkenes has been achieved under mild conditions, providing a variety of chiral spirobarbiturate-cyclopentenes in moderate to excellent yields with moderate to excellent diastereo- and enantioselectivities.
引用
收藏
页码:2867 / 2872
页数:6
相关论文
共 50 条
  • [21] Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3+2] annulation of the Morita-Baylis-Hillman carbonates with pyrazoloneyldiene oxindoles
    Zhang, Jing
    Chan, Wai-Lun
    Chen, Ligong
    Ullah, Nisar
    Lu, Yixin
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2210 - 2214
  • [22] Phosphine-catalyzed [3+2] cycloaddition of Morita-Baylis-Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
    Zenkov, I. S.
    Abel, A. S.
    Averin, A. D.
    Butov, G. M.
    Beletskaya, I. P.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (05) : 880 - 884
  • [23] 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
  • [24] Tertiary Amine-Catalyzed Chemoselective and Asymmetric [3+2] Annulation of Morita-Baylis-Hillman Carbonates of Isatins with Propargyl Sulfones
    Peng, Jing
    Huang, Xin
    Jiang, Lin
    Cui, Hai-Lei
    Chen, Ying-Chun
    ORGANIC LETTERS, 2011, 13 (17) : 4584 - 4587
  • [25] Phosphine-Catalyzed Diastereoselective [3+3] Annulation of Morita-Baylis-Hillman Carbonates with C,N-Cyclic Azomethine Imines
    Zhang, Lei
    Yang, Wenjun
    Zhou, Leijie
    Liu, Honglei
    Huang, Jiaxing
    Xiao, Yumei
    Guo, Hongchao
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3377 - 3388
  • [26] Chiral phosphine-catalyzed enantioselective construction of γ-butenolides through substitution of Morita-Baylis-Hillman acetates with 2-trimethylsilyloxy furan
    Jiang, Ying-Qing
    Shi, Yong-Ling
    Shi, Min
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) : 7202 - +
  • [27] Highly diastereo- and enantioselective [3+2] annulation of isatin-derived Morita-Baylis-Hillman carbonates with trifluoropyruvate catalyzed by tertiary amines
    Zhong, Neng-Jun
    Wei, Feng
    Xuan, Qing-Qing
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    CHEMICAL COMMUNICATIONS, 2013, 49 (94) : 11071 - 11073
  • [28] Highly Regio-and Diastereoselective [3+2]-Annulation Reaction of Morita-Baylis-Hillman Carbonates with Pyrazolones Catalyzed by Tertiary Phosphines
    Zheng, Weiping
    Li, Yuming
    Zhang, Jiayong
    Du, Siyi
    Miao, Zhiwei
    SYNTHESIS-STUTTGART, 2017, 49 (16): : 3676 - 3685
  • [29] Phosphine-catalyzed asymmetric [3+2] annulation of chalcones with allenoates for enantioselective synthesis of functionalized cyclopentenes
    Gao, Zhenzhen
    Wang, Chang
    Yuan, Chunhao
    Zhou, Leijie
    Sun, Zhanhu
    Xiao, Yumei
    Guo, Hongchao
    RSC ADVANCES, 2015, 5 (127): : 105359 - 105362
  • [30] Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita-Baylis-Hillman carbonates
    Wang, De
    Yang, Yuan-Liang
    Jiang, Jia-Jun
    Shi, Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (35) : 7158 - 7166