Palladium-catalyzed [3+2] cycloaddition of alkylidenecyclopropanes with imines

被引:87
|
作者
Oh, BH
Nakamura, I
Saito, S
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Res Ctr Organ Resources & Mat Chem, Inst Chem React Sci, Sendai, Miyagi 9808578, Japan
关键词
alkylidenecyclopropane; imine; palladium catalysts; cycloaddition; pyrrolidine;
D O I
10.1016/S0040-4039(01)01206-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylidenecyclopropanes react with N-tosylimines in toluene in the presence of a catalytic amount of Pd(PPh3)(4) to afford the corresponding [3+2] cycloaddition products, pyrrolidine derivatives, in good to excellent yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6203 / 6205
页数:3
相关论文
共 50 条
  • [1] Synthesis of 3-methylenepyrrolidines by palladium-catalyzed [3+2] cycloaddition of alkylidenecyclopropanes with imines
    Oh, BH
    Nakamura, I
    Saito, S
    Yamamoto, Y
    HETEROCYCLES, 2003, 61 : 247 - +
  • [2] 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
  • [3] 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 - +
  • [4] Novel [3+2] cycloaddition of alkylidenecyclopropanes with aldehydes catalyzed by palladium
    Nakamura, I
    Oh, BH
    Saito, S
    Yamamoto, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (07) : 1298 - +
  • [5] Enantioselective Construction of Pyrrolidines by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with Imines
    Trost, Barry M.
    Silverman, Steven M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) : 4941 - 4954
  • [6] Palladium-Catalyzed [3+2] Cycloaddition of Activated Butadienylcyclopropanes
    Yang, Zhi-Xiong
    Wei, Yu-Qing
    Yang, Cun
    Li, Yun-Fan
    Ding, Chang-Hua
    Xu, Bin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (01)
  • [7] Palladium-Catalyzed [3+2] Cycloaddition of Vinylcyclopropane and Ketones
    Ding, Wen-Ping
    Du, Juan
    Liu, Xiu-Yan
    Chen, Di
    Ding, Chang-Hua
    Deng, Qing-Hai
    Hou, Xue-Long
    SYNLETT, 2019, 30 (08) : 947 - 950
  • [8] 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
  • [9] Palladium-catalyzed [4+3] intramolecular cycloaddition of alkylidenecyclopropanes and dienes
    Gulias, Moises
    Duran, Juan
    Lopez, Fernando
    Castedo, Luis
    Mascarenas, Jose L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) : 11026 - +
  • [10] Palladium-catalyzed intramolecular [3C+2C] cycloaddition of alkylidenecyclopropanes to allenes
    Trillo, Beatriz
    Gulias, Moises
    Lopez, Fernando
    Castedo, Luis
    Mascarenas, Jose L.
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2381 - 2384