Palladium-catalyzed asymmetric (4+3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

被引:11
|
作者
Meng, Yinggao [1 ]
Song, Manman [1 ]
Wang, Yue [1 ]
Wang, Yuxin [1 ]
Li, Er-Qing [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINE; ALKENES;
D O I
10.1039/d3qo00501a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Bronsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.
引用
收藏
页码:2648 / 2652
页数:5
相关论文
共 50 条
  • [31] Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines
    Trost, Barry M.
    Silverman, Steven M.
    Stambuli, James P.
    Journal of the American Chemical Society, 2007, 129 (41): : 12398 - 12399
  • [32] Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with Imines
    Trost, Barry M.
    Silverman, Steven M.
    Stambuli, James P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12398 - +
  • [33] Palladium-catalyzed asymmetric [3+2] trimethylenemethane cycloaddition reactions
    Trost, Barry M.
    Stambuli, James P.
    Silverman, Steven M.
    Schworer, Ulrike
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) : 13328 - 13329
  • [34] 4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed (4+3) cycloaddition of azomethine imines
    Tang, Yi
    Zhang, Rulei
    Dong, Yujie
    Yu, Songcheng
    Wu, Yongjun
    Xiao, Yumei
    Guo, Hongchao
    CHEMICAL COMMUNICATIONS, 2024, 60 (11) : 1436 - 1439
  • [35] Sulfone as a Transient Activating Group in the Palladium-Catalyzed Asymmetric [4+3] Cycloaddition of Trimethylenemethane Enabling the Enantioselective Synthesis of Fused Azepines
    Liu, Yang-Zi
    Wang, Zhongao
    Huang, Zesheng
    Yang, Wu-Lin
    Deng, Wei-Ping
    ORGANIC LETTERS, 2021, 23 (03) : 948 - 952
  • [36] Remote regioselective organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethyl isatin ketimines with cyclic 2,4-dienones
    Zou, Chuncheng
    Han, Yuanyuan
    Zeng, Chuikun
    Zhang, Tony Y.
    Ye, Jinxing
    Song, Gonghua
    CHINESE CHEMICAL LETTERS, 2020, 31 (02) : 377 - 380
  • [37] Remote regioselective organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethyl isatin ketimines with cyclic 2,4-dienones
    Chuncheng Zou
    Yuanyuan Han
    Chuikun Zeng
    Tony Y.Zhang
    Jinxing Ye
    Gonghua Song
    ChineseChemicalLetters, 2020, 31 (02) : 377 - 380
  • [38] Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3+2] Trimethylenemethane Cycloaddition
    Trost, Barry M.
    Bringley, Dustin A.
    Zhang, Ting
    Cramer, Nicolai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) : 16720 - 16735
  • [39] Palladium-catalyzed asymmetric [3+2] methylene-trimethylenemethane cycloaddition reactions
    Trost, Barry M.
    Maruniak, Autumn
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [40] Elaboration of phosphoramidite ligands enabling palladium-catalyzed diastereo-and enantioselective all carbon [4+3]cycloaddition
    Xing Zheng
    Hao Sun
    Wu-Lin Yang
    Wei-Ping Deng
    Science China(Chemistry), 2020, 63 (07) : 911 - 916