Palladium-Catalyzed Regioselective [3+2] Cycloadditions of α,β-Unsaturated Imines with Vinylethylene Carbonates: Access to Oxazolidines

被引:0
作者
Wang, Yuanbo [1 ]
Wang, Yue [2 ]
Sun, Tong [1 ]
Liu, Qinglin [1 ]
Li, Er-Qing [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[2] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol CAIST, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
palladium catalysis; 3+2] cycloaddition; alpha; beta-unsaturated imines; vinylethylene carbonates; oxazolidines; DECARBOXYLATIVE CYCLOADDITION; CONSTRUCTION; ANNULATION; YLIDES;
D O I
10.3390/catal14080508
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We reported palladium-catalyzed regioselective [3+2] cycloadditions of alpha,beta-unsaturated imines with vinylethylene carbonates, providing the desired oxazolidines in moderate-to-high yields. This reaction provides a facile route for the highly regioselective synthesis of functional oxazolidines. The synthetic utility of the current method was also demonstrated by a gram-scale reaction.
引用
收藏
页数:12
相关论文
共 35 条
  • [31] Asymmetric catalysis with chiral oxazolidine ligands
    Wolf, Christian
    Xu, Hanhui
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (12) : 3339 - 3350
  • [32] Sterically and Temperature Controlled Divergent Cycloadditions of α,β-Unsaturated Imines with Vinylethylene Carbonates: Insights from Experimental and DFT Studies
    Xie, Xiaolong
    Yuan, Dandan
    Ma, Ben
    Jin, Jiaming
    Wang, Enpeng
    Zhou, Wenyi
    Hu, Yaowen
    Hu, Lihong
    Wang, Junwei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1168 - 1178
  • [33] Renaissance of pyridine-oxazolines as chiral ligands for asymmetric catalysis
    Yang, Guoqiang
    Zhang, Wanbin
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (05) : 1783 - 1810
  • [34] Pd-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Imines
    Yang, Lei
    Khan, Ajmal
    Zheng, Renfeng
    Jin, Long Yi
    Zhang, Yong Jian
    [J]. ORGANIC LETTERS, 2015, 17 (24) : 6230 - 6233
  • [35] Formal [5+3] Cycloaddition of Zwitterionic Allylpalladium Intermediates with Azomethine Imines for Construction of N,O-Containing Eight-Membered Heterocycles
    Yuan, Chunhao
    Wu, Yang
    Wang, Dongqi
    Zhang, Zhenhua
    Wang, Chang
    Zhou, Leijie
    Zhang, Cheng
    Song, Baoan
    Guo, Hongchao
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 652 - 658