Catalytic asymmetric synthesis of pyrrolidine derivatives bearing heteroatom-substituted quaternary stereocenters

被引:20
|
作者
Wang, Zhi-Peng [1 ]
Wu, Qi [1 ]
Jiang, Jia [1 ]
Li, Zi-Rui [1 ]
Peng, Xiao-Jiao [1 ]
Shao, Pan-Lin [1 ]
He, Yun [1 ]
机构
[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, 55 Daxuecheng South Rd, Chongqing 401331, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 01期
基金
中国国家自然科学基金;
关键词
FORMAL 3+2 CYCLOADDITION; N-HETEROCYCLIC CARBENES; AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; ALDOL REACTIONS; STEREOSELECTIVE-SYNTHESIS; METHYL ISOCYANOACETATE; ALPHA-ISOCYANOACETATES; MICHAEL ADDITION;
D O I
10.1039/c7qo00692f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective [3 + 2] cycloaddition of heteroatom-substituted alkenes with alpha-substituted isocyanoacetates has been developed. The resulting cycloadducts could be further transformed to access a number of structurally diverse and biologically important pyrrolidine derivatives which bear sulfur-or oxygen-substituted quaternary stereocenters. Excellent reactivity and enantioselectivity were obtained for a broad range of substrates.
引用
收藏
页码:36 / 40
页数:5
相关论文
共 50 条
  • [31] Catalytic asymmetric construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements
    Zhang, Wande
    Wei, Shiqiang
    Wang, Wenyao
    Qu, Jingping
    Wang, Baomin
    CHEMICAL COMMUNICATIONS, 2021, 57 (53) : 6550 - 6553
  • [32] Organocatalytic asymmetric synthesis of highly substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position+
    Mukhopadhyay, Soumendranath
    Pan, Subhas Chandra
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (48) : 9349 - 9353
  • [33] Catalytic Asymmetric Electrophilic Amination Reactions To Form Nitrogen-Bearing Tetrasubstituted Carbon Stereocenters
    Zhou, Feng
    Liao, Fu-Min
    Yu, Jin-Sheng
    Zhou, Jian
    SYNTHESIS-STUTTGART, 2014, 46 (22): : 2983 - 3003
  • [34] Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF3 Stereogenic Center
    Huang, Yi-Yong
    Yang, Xing
    Chen, Zhuo
    Verpoort, Francis
    Shibata, Norio
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (24) : 8664 - 8684
  • [35] Catalytic asymmetric synthesis of highly substituted pyrrolizidines
    Lim, Andrew D.
    Codelli, Julian A.
    Reisman, Sarah E.
    CHEMICAL SCIENCE, 2013, 4 (02) : 650 - 654
  • [36] Catalytic Asymmetric Synthesis of Substituted Morpholines and Piperazines
    Zhai, Huimin
    Borzenko, Andrey
    Lau, Ying Yin
    Ahn, Shin Hye
    Schafer, Laurel L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) : 12219 - 12223
  • [37] Squaramide-Catalyzed Asymmetric Mannich Reactions of Azlactones with (satin-Derived Ketimines: Access to α,β-Diamino Acid Derivatives Bearing Vicinal Quaternary Stereocenters
    Li, Zhanhuan
    Peng, Jingyi
    He, Chonglong
    Xu, Jianfeng
    Ren, Hongjun
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) : 3894 - 3901
  • [38] Stereodivergent Synthesis of Carbocyclic Quaternary α-Amino Acid Derivatives Containing Two Contiguous Stereocenters
    Fu, Cong
    Xiong, Qi
    Xiao, Lu
    He, Ling
    Bai, Tian
    Zhang, Zongpeng
    Dong, Xiu-Qin
    Wang, Chun-Jiang
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (09) : 1059 - 1065
  • [39] Asymmetric Construction of Vicinal Stereocenters Containing Quaternary and Tertiary Carbons: Application to the Formal Synthesis of (-)-Chenopodene
    Harada, Kenichi
    Ibaragi, Daisuke
    Edazawa, Yui
    Sakashita, Masanori
    Nakata, Ayane
    Kubo, Miwa
    Carter, Rich G.
    Fukuyama, Yoshiyasu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 420 - 423
  • [40] Organocatalytic asymmetric synthesis of 3(2H)-furanones with adjacent quaternary and tertiary stereocenters
    He, Wujun
    Jing, Linhai
    Qin, Dabin
    Wang, Rongming
    Xie, Xiaohua
    Wu, Song
    TETRAHEDRON LETTERS, 2013, 54 (47) : 6363 - 6365