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

页数：5

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
[J]. ORGANIC LETTERS, 2019, 21 (05) : 1388 - 1392
[2] Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis
Chatterjee, Tanmay
Cho, Ji Young
Cho, Eun Jin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 6995 - 7000
[3] Synthesis of fluoroalkylated alkynes via visible-light photocatalysis
Iqbal, Naila
Iqbal, Naeem
Han, Sung Su
Cho, Eun Jin
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (07) : 1758 - 1762
[4] Synthesis of Isothiocyanates from Primary Amines via Visible-Light Photocatalysis
Ma, Jinglin
Li, Fengxi
Wang, Chunyu
Wang, Zhi
Du, Chuang
Wang, Lei
[J]. ORGANIC LETTERS, 2023, 25 (30) : 5692 - 5696
[5] Visible-light promoted isomerization of vinylnitrones to vinyloxaziridines
Moura-Letts, Gustavo
Zinsky, Amy
Austin, Brooke
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[6] 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
[J]. SYNLETT, 2024, 35 (03) : 325 - 329
[7] Intracellular Synthesis of Indoles Enabled by Visible-Light Photocatalysis
D'Avino, Cinzia
Gutierrez, Sara
Feldhaus, Max J.
Tomas-Gamasa, Maria
Mascarenas, Jose Luis
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (05) : 2895 - 2900
[8] Polyoxometalate built-in conjugated microporous polymers for visible-light heterogeneous photocatalysis
Li, Yusen
Liu, Mingxuan
Chen, Long
[J]. JOURNAL OF MATERIALS CHEMISTRY A, 2017, 5 (26) : 13757 - 13762
[9] Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
Marzo, Leyre
Pagire, Santosh K.
Reiser, Oliver
Koenig, Burkhard
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) : 10034 - 10072
[10] Visible-light photocatalysis by modified titania
Kisch, H
Macyk, W
[J]. CHEMPHYSCHEM, 2002, 3 (05) : 399 - +

← 1 2 3 4 5 →