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.
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页数：5
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