Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

被引：2
|
作者：
Trieu, Phillip [1 ]
Filkin, William H. [1 ]
Pinarci, Ali [1 ]
Tobias, Elisa M. [1 ]
Madiu, Rufai [1 ]
Dellosso, Brandon [1 ]
Roldan, Justin [1 ]
Das, Pulakesh [1 ]
Austin, Brooke E. [1 ]
Moura-Letts, Gustavo [1 ]
机构：
[1] Rowan Univ, Dept Chem & Biochem, 201 Mull Hill Rd, Glassboro, NJ 08028 USA
来源：
CHEMPHOTOCHEM | 2023年 / 7卷 / 03期
基金：
美国国家科学基金会;
关键词：
dipolar cycloadditions; heterocycles; isoxazolidines; photocatalysis; vinyl nitrones; TRANSFER RADICAL-ADDITION; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; PHOTOREDOX CATALYSIS; ZETEKITOXIN-AB; METHACROLEIN; NITROSOARENES; 2H-AZIRINES; NITRONES; ALKENES;
D O I：
10.1002/cptc.202200277
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)(3)Cl-2, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.
引用
收藏
页数：5
相关论文
共 50 条
  • [1] Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis
    Haun, Graham
    Paneque, Alyson N.
    Almond, David W.
    Austin, Brooke E.
    Moura-Letts, Gustavo
    ORGANIC LETTERS, 2019, 21 (05) : 1388 - 1392
  • [2] Visible-Light-Promoted Synthesis of Vinyloxaziridines from Conjugated Carbonyls
    Austin, Brooke E.
    Palner, Ryan P.
    Tobias, Elissa M.
    Madiu, Rufai
    Doran, Erin L.
    Doran, Jenna M.
    Howard, Amari M.
    Stroud, James L.
    Rossi, Morgan E.
    Moskovitz, Dylan A.
    Rivera, Dominic A.
    Mullen, Michael D.
    Zinsky, Amy H.
    Rosario, Rose A.
    Moura-Letts, Gustavo
    SYNLETT, 2024, 35 (03) : 325 - 329
  • [3] Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
    Marzo, Leyre
    Pagire, Santosh K.
    Reiser, Oliver
    Koenig, Burkhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) : 10034 - 10072
  • [4] Frontiers in Radical Fluoromethylation by Visible-Light Organic Photocatalysis
    Koike, Takashi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (04) : 529 - 537
  • [5] Deracemization Enabled by Visible-Light Photocatalysis
    Shi, Qinglong
    Ye, Juntao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) : 4998 - 5001
  • [6] Protodesilylation of Arylsilanes by Visible-Light Photocatalysis
    Kuhlmann, Jan H.
    Uygur, Mustafa
    Mancheno, Olga Garcia
    ORGANIC LETTERS, 2022, 24 (08) : 1689 - 1694
  • [7] Integrating TEMPO and Its Analogues with Visible-Light Photocatalysis
    Lang, Xianjun
    Zhao, Jincai
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (06) : 599 - 613
  • [8] Hydrodifluoromethylation of unactivated alkenes enabled by Visible-Light Photocatalysis
    Jha, Avishek Kumar
    Kumar, Vivek
    Perumandla, Sanjay Kumar
    Yatham, Veera Reddy
    CHEMPHOTOCHEM, 2024, 8 (06)
  • [9] Photocatalytic nanodiodes for visible-light photocatalysis
    Kim, HG
    Borse, PH
    Choi, WY
    Lee, JS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) : 4585 - 4589
  • [10] Bioorthogonal Synthetic Chemistry Enabled by Visible-Light Photocatalysis
    Mato, Mauro
    Fernandez-Gonzalez, Xulian
    DAvino, Cinzia
    Tomas-Gamasa, Maria
    Mascarenas, Jose L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (47)
12345