Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines

被引：13
作者：
Gao, Xing [1 ,2 ]
Zhu, Dongyu [1 ,2 ]
Jiang, Feng [1 ,2 ]
Liao, Jianning [1 ,2 ]
Wang, Wei [3 ]
Wu, Yongjun [3 ]
Zheng, Lufei [4 ]
Guo, Hongchao [1 ,2 ,5 ]
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
[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China
[4] Chinese Acad Agr Sci, Inst Qual Stand & Testing Technol Agroprod, Beijing 100081, Peoples R China
[5] China Agr Univ, Dept Nutr & Hlth, Beijing 100193, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 22期
基金：
中国国家自然科学基金;
关键词：
DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; AZOMETHINE YLIDES; TERTIARY; ACCESS; FERMENTATION; HETEROCYCLES; SPIROKETALS; ALLYLATION; ANNULATION;
D O I：
10.1039/d1ob00614b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd(2)dba(3)center dot CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.
引用
收藏
页码：4877 / 4881
页数：5
相关论文
共 50 条
  • [41] Asymmetric palladium-catalyzed decarboxylative [3+2] cycloaddition: straightforward construction of chiral spiro-heterocyclic scaffolds
    Zhang, Ke
    You, Pengyuan
    Zuo, Sheng
    Tao, Yuan
    Chen, Fen-er
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (05) : 1479 - 1483
  • [42] Selective Aza Diels-Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines
    Kiran, I. N. Chaithanya
    Reddy, R. Santhosh
    Lagishetti, Chandraiah
    Xu, Huacheng
    Wang, Zhen
    He, Yun
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) : 1823 - 1832
  • [43] A Highly Regio- and Diastereoselective Phosphane-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic N-Acyl Ketimines
    Yang, Li-Jun
    Cai, Hua
    Nie, Jing
    Ma, Jun-An
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4434 - 4442
  • [44] Palladium-Catalyzed [3+2]-C C/N C Bond-Forming Annulation
    Liu, Yang
    Mao, Zhongyi
    Pradal, Alexandre
    Huang, Pei-Qiang
    Oble, Julie
    Poli, Giovanni
    ORGANIC LETTERS, 2018, 20 (13) : 4057 - 4061
  • [45] Palladium-catalyzed [4+3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides
    Dai, Wenhao
    Li, Chunpu
    Liu, Yichu
    Han, Xu
    Li, Xingjun
    Chen, Kaixian
    Liu, Hong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18) : 2612 - 2617
  • [46] An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(I)
    Zhou, Minghui
    Su, Qin
    Addepalli, Yesu
    He, Yun
    Wang, Zhen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (16) : 2923 - 2931
  • [47] Palladium-Catalyzed [4+2] Cycloaddition of Hydroxy-Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans
    Xu, Jiaqing
    Shi, Wangyu
    Liu, Min
    Liao, Jianning
    Wang, Wei
    Wu, Yongjun
    Guo, Hongchao
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (12) : 2060 - 2066
  • [48] Palladium-Catalyzed Tandem Dehydrogenative [4+2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
    Sun, Manman
    Chen, Weida
    Xia, Xiangyu
    Shen, Guodong
    Ma, Yongmin
    Yang, Jianguo
    Ding, Hanfeng
    Wang, Zhiming
    ORGANIC LETTERS, 2020, 22 (08) : 3229 - 3233
  • [49] Palladium-Catalyzed Regio- and Stereoselective Cross-Coupling of Vinylethylene Carbonates with Ketimine Esters to Generate (Z)-Tri- and Tetra-substituted Allylic Amino Acid Derivatives
    Ke, Miaolin
    Liu, Zhigang
    Huang, Guanxin
    Wang, Jiaqi
    Tao, Yuan
    Chen, Fener
    ORGANIC LETTERS, 2020, 22 (11) : 4135 - 4140
  • [50] Palladium-Catalyzed [3+2] Annulation of Naphthalimide Acceptors and Thiophene Donors
    Shoyama, Kazutaka
    Mahl, Magnus
    Niyas, M. A.
    Ebert, Markus
    Kachler, Valentin
    Keck, Christoph
    Wuerthner, Frank
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (01) : 142 - 149
12345