Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids

被引:12
作者
Zhao, Yang [1 ,2 ]
Wang, Xiao-Qing [1 ]
Yu, Yan-Jiang [1 ]
Zhou, Yong-Gui [1 ,3 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE SYNTHESIS; OPTICAL RESOLUTION; PLANAR; EFFICIENT; PARACYCLOPHANES; ALDIMINES;
D O I
10.1021/acs.joc.0c02509
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile method for kinetic resolution of [2.2]paracyclophane-derived cyclic N-sulfonylimines based on palladium-catalyzed addition of arylboronic acids was developed, giving two kinds of planar chiral [2.2]paracyclophane derivatives in excellent diastereoselectivities and up to 99% of enantioselectivities with high selectivity factors (s up to 128).
引用
收藏
页码:1262 / 1272
页数:11
相关论文
共 22 条
  • [1] Nickel-Catalyzed Asymmetric Hydrogenation for Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines
    Zhao, Yang
    Ding, Yi-Xuan
    Wu, Bo
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) : 10788 - 10798
  • [2] Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids
    Zhao, Yang
    Wang, Han
    Wu, Bo
    Zhou, Yong-Gui
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (24) : 3956 - 3960
  • [3] Dearomatization of [2.2]Paracyclophane-Derived N-Sulfonylimines through Cyclopropanation with Sulfur Ylides
    Zhao, Yang
    Li, Xiang
    Deng, Wen-Hao
    Wu, Bo
    Liao, Rong-Zhen
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01) : 321 - 329
  • [4] Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles
    Shockley, Samantha E.
    Holder, Jeffrey C.
    Stoltz, Brian M.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (08) : 974 - 981
  • [5] Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones
    Holder, Jeffrey C.
    Goodman, Emmett D.
    Kikushima, Kotaro
    Gatti, Michele
    Marziale, Alexander N.
    Stoltz, Brian M.
    TETRAHEDRON, 2015, 71 (35) : 5781 - 5792
  • [6] Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors
    Holder, Jeffrey C.
    Marziale, Alexander N.
    Gatti, Michele
    Mao, Bin
    Stoltz, Brian M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (01) : 74 - 77
  • [7] Synthesis of chiral quaternary fluorinated cyclic sulfamidates via palladium-catalyzed arylation with arylboronic acids
    Chen, Mu-Wang
    Mao, Xuechun
    Ji, Yue
    Yuan, Jianjun
    Deng, Zhihong
    Peng, Yiyuan
    TETRAHEDRON LETTERS, 2019, 60 (48)
  • [8] Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N-Terminal Guanidinylated Helical Peptide
    Tian, Jiaqi
    Tamaribuchi, Kenya
    Yoshikawa, Isao
    Kudo, Kazuaki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (16)
  • [9] Palladium-Catalyzed Addition of Arylboronic Acids to para-Quinone Methides for Preparation of Diarylacetates
    Zhuge, Ruijing
    Wu, Liang
    Quan, Mao
    Butt, Nicholas
    Yang, Guoqiang
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 1028 - 1036
  • [10] Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane
    Akagawa, Kengo
    Nishi, Nobuhiro
    Yoshikawa, Isao
    Kudo, Kazuaki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5055 - 5059