Enantioselective Cobalt-Catalyzed Sequential Nazarov Cyclization/Electrophilic Fluorination: Access to Chiral α-Fluorocyclopentenones

被引：29
|
作者：
Zhang, Heyi [1 ]
Cheng, Biao [1 ]
Lu, Zhan [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 13期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC FLUORINATION; BETA-KETOESTERS; MEDICINAL CHEMISTRY; RECENT PROGRESS; KETO-ESTERS; CYCLIZATION; TRIFLUOROMETHYLATION; CYCLOPENTENONES; CONSTRUCTION; DERIVATIVES;
D O I：
10.1021/acs.orglett.8b01597
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A newly designed thiazoline iminopyridine ligand for enantioselective cobalt-catalyzed sequential Nazarov cyclization/electrophilic fluorination was developed. Various chiral alpha-fluorocyclopentenones were prepared with good yields and diastereo- and enantioselectivities. Further derivatizations could be easily carried out to provide chiral cyclopentenols with three contiguous stereocenters. Furthermore, a direct deesterification of fluorinated products could afford chiral alpha-single fluorine-substituted cyclopentenones.
引用
收藏
页码：4028 / 4031
页数：4
相关论文
共 50 条
  • [21] Enantioselective Palladium(0)-Catalyzed Nazarov-Type Cyclization
    Kitamura, Kei
    Shimada, Naoyuki
    Stewart, Craig
    Atesin, Abdurrahman C.
    Atesin, Tuelay A.
    Tius, Marcus A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (21) : 6288 - 6291
  • [22] Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination
    Zhu, Chuan-Le
    Maeno, Mayaka
    Zhang, Fa-Guang
    Shigehiro, Taiki
    Kagawa, Takumi
    Kawada, Kosuke
    Shibata, Norio
    Ma, Jun-An
    Cahard, Dominique
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (29) : 6501 - 6505
  • [23] Cobalt-catalyzed isocyanide insertion cyclization to dihydrobenzoimidazotriazins
    Ahmadi, Fereshteh
    Mirzaei, Peiman
    Bazgir, Ayoob
    TETRAHEDRON LETTERS, 2017, 58 (45) : 4281 - 4284
  • [24] Cobalt-Catalyzed Enantioselective Hydrotrifluoromethoxylation of Aromatic Alkenes
    Si, Yafeng
    Liu, Yuntao
    Zhou, Fan
    Fang, Lei
    Wu, Kang
    Luan, Yu-Xin
    Chen, Li
    Tang, Pingping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [25] Highly Enantioselective Cobalt-Catalyzed Hydrosilylation of Alkenes
    Cheng, Biao
    Lu, Peng
    Zhang, Heyi
    Cheng, Xinpeng
    Lu, Zhan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (28) : 9439 - 9442
  • [26] Recent developments in enantioselective cobalt-catalyzed transformations
    Pellissier, Helene
    COORDINATION CHEMISTRY REVIEWS, 2018, 360 : 122 - 168
  • [27] Enantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates
    Dong, Wenke
    Liu, Zheming
    Bai, Anbang
    Zhang, Xiaoyu
    Han, Peiwen
    He, Jingyi
    Li, Chenchen
    ORGANIC LETTERS, 2025, 27 (08) : 1895 - 1900
  • [28] Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes
    Wei, Lin-Wen
    Ma, Zhan-Cai
    Wang, Zhao-Qing
    Zhao, Yu
    Huang, Yuan
    SYNTHESIS-STUTTGART, 2023, 55 (23): : 3954 - 3960
  • [29] Cobalt-Catalyzed Enantioselective Hydroboration of α-Substituted Acrylates
    Patil, Manoj D.
    Ghosh, Kiron Kumar
    Rajanbabu, T. V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (10) : 6604 - 6617
  • [30] Cobalt-Catalyzed Enantioselective Hydroboration/Cyclization of 1,7-Enynes: Asymmetric Synthesis of Chiral Quinolinones Containing Quaternary Stereogenic Centers
    Wu, Caizhi
    Liao, Jiayu
    Ge, Shaozhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) : 8882 - 8886
12345