Chiral phosphoric acid catalyzed enantioselective inverse-electron-demand oxa-Diels-Alder reactions to synthesize chiral tricyclic tetrahydropyran derivatives

被引：0
|
作者：
Tang, Cong-Yun [1 ,3 ]
Wu, Jie [3 ,4 ]
Ji, Feng-Ting [1 ,3 ]
Tian, Fang [2 ]
Peng, Lin [1 ]
Wang, Liang-Liang [3 ]
机构：
[1] Shaoyang Univ, Sch Food & Chem Engn, Shaoyang 422000, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Prov, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Chi, Kunming Inst Bot, Kunming 650201, Peoples R China
[4] Univ Chinese Acad Sci, Beijing 101408, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 11卷 / 01期
关键词：
ORTHO-QUINONE METHIDES; BRONSTED ACID; CYCLOADDITIONS; ACTIVATION;
D O I：
10.1039/d3qo01615c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of enantioenriched tricyclic tetrahydropyran derivatives were achieved through chiral phosphoric acid catalyzed intramolecular inverse electron demand oxa-Diels-Alder (IEDODA) reactions, with good yields (up to 95%) and excellent stereocontrol (>20 : 1 dr, up to 99% ee). The achievement of such high enantioselectivity was ascribed to the rationally designed remote dual hydrogen bonding interaction, by which the conformation of the flexible substrate was well arranged by the catalyst in a reactive and stereoselective manner to participate in the transformation.
引用
收藏
页码：211 / 216
页数：6
相关论文
共 50 条
  • [1] Chiral Phosphoric Acid Catalyzed Inverse-Electron-Demand Aza-Diels-Alder Reaction of Isoeugenol Derivatives
    He, Long
    Bekkaye, Mathieu
    Retailleau, Pascal
    Masson, Geraldine
    [J]. ORGANIC LETTERS, 2012, 14 (12) : 3158 - 3161
  • [2] Enantioselective Synthesis of Complex Fused Heterocycles through Chiral Phosphoric Acid Catalyzed Intramolecular Inverse-Electron-Demand Aza-Diels-Alder Reactions
    Jarrige, Lucie
    Gandon, Vincent
    Masson, Geraldine
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (06) : 1406 - 1413
  • [3] A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand oxa-Diels-Alder reaction of o-quinone methides with fulvenes
    Zhang, Jianlin
    Lin, Lili
    He, Changqiang
    Xiong, Qian
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (01) : 74 - 77
  • [4] Inverse-Electron-Demand oxa-Diels-Alder Reactions of α-Keto-β,γ-unsaturated Esters and α,β-Unsaturated Hydrazones
    Hashimoto, Yoshimitsu
    Ikeda, Takanori
    Ida, Ayako
    Morita, Nobuyoshi
    Tamura, Osamu
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 4245 - 4249
  • [5] Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction
    Hu, Haipeng
    Liu, Yangbin
    Guo, Jing
    Lin, Lili
    Xu, Yali
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (18) : 3835 - 3837
  • [6] Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction of Allylic Ketones through Dienamine Catalysis
    Shi, Ming-Lin
    Zhan, Gu
    Zhou, Su-Lan
    Du, Wei
    Chen, Ying-Chun
    [J]. ORGANIC LETTERS, 2016, 18 (24) : 6480 - 6483
  • [7] Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions
    Varlet, Thomas
    Gelis, Coralie
    Retailleau, Pascal
    Bernadat, Guillaume
    Neuville, Luc
    Masson, Géraldine
    [J]. Advanced Materials, 2020, 132 (22) : 8569 - 8574
  • [8] Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reaction of α,β-Substituted Acroleins
    Hatano, Manabu
    Sakamoto, Tatsuhiro
    Mochizuki, Takuya
    Ishihara, Kazuaki
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (07) : 1061 - 1066
  • [9] Chiral Bisguanidine-Catalyzed Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Chalcones with Azlactones
    Dong, Shunxi
    Liu, Xiaohua
    Chen, Xiaohong
    Mei, Fang
    Zhang, Yulong
    Gao, Bo
    Lin, Lili
    Feng, Xiaoming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10650 - 10651
  • [10] Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels-Alder Reactions
    Varlet, Thomas
    Gelis, Coralie
    Retailleau, Pascal
    Bernadat, Guillaume
    Neuville, Luc
    Masson, Geraldine
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (22) : 8491 - 8496
12345