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
  • [41] Rhodium-Catalyzed Asymmetric Reductive Cyclization of Heteroatom-Linked 5-Alkynals with Heteroatom-Substituted Acetaldehydes
    Tanaka, Rie
    Noguchi, Keiichi
    Tanaka, Ken
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1238 - +
  • [42] Catalytic asymmetric addition to cyclic N-acyl-iminium: access to sulfone-bearing contiguous quaternary stereocenters
    Bhosale, Viraj A.
    Cisarova, Ivana
    Kamlar, Martin
    Vesely, Jan
    CHEMICAL COMMUNICATIONS, 2022, 58 (71) : 9942 - 9945
  • [43] α-Heteroatom-substituted gem-Bisphosphonates: Advances in the Synthesis Prospects for Biomedical Application
    Romanenko, Vadim D.
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (05) : 530 - 615
  • [44] Solution-Phase Synthesis of Heteroatom-Substituted Carbon Scaffolds for Hydrogen Storage
    Jin, Zhong
    Sun, Zhengzong
    Simpson, Lin J.
    O'Neill, Kevin J.
    Parilla, Philip A.
    Li, Yan
    Stadie, Nicholas P.
    Ahn, Channing C.
    Kittrell, Carter
    Tour, James M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) : 15246 - 15251
  • [45] Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation
    Yang, Jianping
    Ponra, Sudipta
    Li, Xingzhen
    Peters, Bram B. C.
    Massaro, Luca
    Zhou, Taigang
    Andersson, Pher G.
    CHEMICAL SCIENCE, 2022, 13 (29) : 8590 - 8596
  • [46] Catalytic Asymmetric Synthesis of Dihydrofurans and Cyclopentenols with Tertiary Stereocenters
    Wu, Zhongtao
    Madduri, Ashoka V. R.
    Harutyunyan, Syuzanna R.
    Minnaard, Adriaan J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 575 - 582
  • [47] Construction of Acyclic Quaternary Carbon Stereocenters by Catalytic Asymmetric Hydroalkynylation of Unactivated Alkenes
    Wang, Zi-Xuan
    Li, Bi-Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (23) : 9312 - 9320
  • [48] Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
    Woldegiorgis, Alemayehu Gashaw
    Han, Zhao
    Lin, Xufeng
    ORGANIC LETTERS, 2021, 23 (17) : 6606 - 6611
  • [49] Asymmetric Synthesis of Multicyclic Spirooxindole Derivatives Bearing Stereogenic Quaternary Carbon Atoms
    Li, Xiaoyi
    Li, Zihao
    Zhang, Rong
    Zhou, Zhen
    Zhang, Yonghui
    Xia, Yi
    Yao, Weijun
    Wang, Zhen
    ORGANIC LETTERS, 2023, 25 (15) : 2642 - 2646
  • [50] Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters
    Su, Yong-Liang
    Li, Yu-Hui
    Chen, Yu-Gen
    Han, Zhi-Yong
    CHEMICAL COMMUNICATIONS, 2017, 53 (12) : 1985 - 1988