Catalytic asymmetric de novo construction of 4-pyrrolin-2-ones via intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones

被引:8
|
作者
Mo, Nan-Nan [1 ,2 ]
Miao, Yu-Hang [1 ,2 ]
Xiao, Xiao [3 ]
Hua, Yuan-Zhao [1 ,2 ]
Wang, Min-Can [1 ,2 ]
Huang, Lihua [1 ,2 ]
Mei, Guang-Jian [1 ,2 ]
机构
[1] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[3] Zhejiang Univ Technol, Inst Pharmaceut Sci & Technol, Hangzhou 310014, Peoples R China
关键词
DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; HETEROCYCLES;
D O I
10.1039/d3cc01194a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chiral phosphoric acid-catalyzed asymmetric intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones has been established. This convergent protocol leads to a facile and enantioselective de novo construction of a wide range of fully substituted 4-pyrrolin-2-ones bearing a fully substituted carbon atom in good yields and with excellent enantioselectivities (26 examples, 72-95% yields and 87-99% ee).
引用
收藏
页码:5902 / 5905
页数:4
相关论文
共 50 条
  • [11] Catalytic asymmetric [3+2] cycloaddition of hydrazones with olefins.
    Yamashita, Y
    Shimizu, H
    Ishitani, H
    Kobayashi, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U219 - U219
  • [12] Total Synthesis of (±)-Minfiensine via a Formal [3+2] Cycloaddition
    Zhang, Chao
    Ji, Wenzhi
    Liu, Yahu A.
    Song, Chun
    Liao, Xuebin
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (04): : 1065 - 1069
  • [13] Methylenecyclopentane annulation via formal [3+2] cycloaddition reaction
    Takahashi, Y
    Tanino, K
    Kuwajima, I
    TETRAHEDRON LETTERS, 1996, 37 (33) : 5943 - 5946
  • [14] Enantioselective de novo construction of 3-oxindoles via organocatalyzed formal [3+2] annulation from simple arylamines
    Wang, Yong
    Li, Yanyan
    Chen, Haohua
    Lan, Yu
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [15] Synthesis of 4-Phosphinylpyrrolidin-3-ones via [3+2] Cycloaddition of Nitrones with Phosphinylallenes
    Hammami, Rayhane
    Maldivi, Pascale
    Philouze, Christian
    Carret, Sebastien
    Darses, Benjamin
    Touil, Soufiane
    Poisson, Jean-Francois
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) : 1385 - 1390
  • [16] Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions
    Lu, Yi-Nan
    Lan, Jin-Ping
    Mao, Yu-Jia
    Wang, Ye-Xin
    Mei, Guang-Jian
    Shi, Feng
    CHEMICAL COMMUNICATIONS, 2018, 54 (96) : 13527 - 13530
  • [17] Synthesis of Chiral Tetrahydrofurans via Catalytic Asymmetric [3+2] Cycloaddition of Heterosubstituted Alkenes with Oxiranes
    Yuan, Xiao
    Lin, Lili
    Chen, Weiliang
    Wu, Wangbin
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03): : 1237 - 1243
  • [18] Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides
    Pandey, Ganesh
    Banerjee, Prabal
    Gadre, Smita R.
    CHEMICAL REVIEWS, 2006, 106 (11) : 4484 - 4517
  • [19] Catalytic asymmetric synthesis of highly functionalized cyclopentenes by a [3+2] cycloaddition
    Davies, HML
    Xiang, BP
    Kong, N
    Stafford, DG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) : 7461 - 7462
  • [20] Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition of Iminoesters with Nitroalkenes
    Arai, Takayoshi
    Yokoyama, Naota
    Mishiro, Asami
    Sato, Hiroyasu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) : 7895 - 7898