Enantioselective synthesis of spiro-N,O-ketals via iridium and Brønsted acid co-catalyzed asymmetric formal [4+2] cycloaddition

被引：5
|
作者：
Xie, Xiang-Qi [1 ]
Li, Xingguang [1 ]
Liu, Pei-Nian [1 ]
机构：
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 11期
基金：
中国国家自然科学基金;
关键词：
ALLYLIC SUBSTITUTION-REACTIONS; SPIROAMINALS; SPIROKETALS; ACCESS; CYCLIZATION; PALLADIUM;
D O I：
10.1039/d3cc05923e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We present an iridium and Br & oslash;nsted acid co-catalyzed enantioselective formal [4+2] cycloaddition reaction of cyclic enamides with 2-(1-hydroxyallyl)phenols. This method yields a wide range of N-unsubstituted spiro-N,O-ketals, with good efficiency (up to 94%) and excellent enantioselectivities (most >95% ee). The protocol features easy scale-up and facile product derivatization.
引用
收藏
页码：1448 / 1451
页数：4
相关论文
共 50 条
  • [21] One-pot synthesis of tetrahydroindoles via a copper catalyzed N-alkynation/[4+2] cycloaddition cascade
    Jiang, Chun
    Yu, Piao-Piao
    Zhang, Qing
    Xu, Hua-Dong
    Shen, Mei-Hua
    CHINESE CHEMICAL LETTERS, 2019, 30 (01) : 266 - 268
  • [22] One-Pot Synthesis of Enantioenriched β-Amino Secondary Amides via an Enantioselective [4+2] Cycloaddition Reaction of Vinyl Azides with N-Acyl Imines Catalyzed by a Chiral Bronsted Acid
    Nakanishi, Taishi
    Kikuchi, Jun
    Kaga, Atsushi
    Chiba, Shunsuke
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (37) : 8230 - 8234
  • [23] Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
    Zou, Huaxu
    Jiang, Jun
    Yi, Niannian
    Fu, Wenqiang
    Deng, Wei
    Xiang, Jiannan
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (12) : 1251 - 1254
  • [24] Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives
    Suarez-Rodriguez, Tatiana
    Suarez-Sobrino, angel L.
    Ballesteros, Alfredo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) : 13079 - 13084
  • [25] Sugar-Assisted Kinetic Resolutions in Metal/Chiral Amine Co-Catalyzed α-Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives
    Zhang, Kaiheng
    Carmo, Chrislaura
    Deiana, Luca
    Grape, Erik Svensson
    Inge, A. Ken
    Cordova, Armando
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (53)
  • [26] Synthesis of Fluorinated 4-Aminopyrimidines via Brønsted Acid Mediated [2+2+2] Cycloaddition of β-Trifluoromethyl-1,3-enynamides with Nitriles
    Zeng, Qin
    Li, Jintong
    Xiao, Yuanjing
    SYNTHESIS-STUTTGART, 2025, 57 (07): : 1339 - 1345
  • [27] Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds
    Liu, Qiang
    Chen, Xiang-Yu
    Li, Sun
    Vetica, Fabrizio
    Raabe, Gerhard
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2018, 50 (01): : 127 - 133
  • [28] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes
    Asao, N
    Nogami, T
    Lee, S
    Yamamoto, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10921 - 10925
  • [29] Synthesis of Benzofuran-fused 1,4-Dihydropyridines via Bifunctional Squaramide-catalyzed Formal [4+2] Cycloaddition of Azadienes with Malononitrile
    Gu, Zheng
    Wu, Bo
    Jiang, Guo-Fang
    Zhou, Yong-Gui
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) : 1130 - 1134
  • [30] Enantioselective Copper-Catalyzed Formal [4+2] Cycloaddition of o-Aminophenol Derivatives with Propargylic Esters for Synthesis of Optically Active 3,4-Dihydro-2H-1,4-benzoxazines
    Liu, Zhen-Ting
    Wang, Ya-Hui
    Zhu, Fu-Lin
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2016, 18 (05) : 1190 - 1193
12345