Visible-Light-Promoted Synthesis of Vinyloxaziridines from Conjugated Carbonyls

被引：1

作者：

Austin, Brooke E. ^{[1
]}

Palner, Ryan P. ^{[1
]}

Tobias, Elissa M. ^{[1
]}

Madiu, Rufai ^{[1
]}

Doran, Erin L. ^{[1
]}

Doran, Jenna M. ^{[1
]}

Howard, Amari M. ^{[1
]}

Stroud, James L. ^{[1
]}

Rossi, Morgan E. ^{[1
]}

Moskovitz, Dylan A. ^{[1
]}

Rivera, Dominic A. ^{[1
]}

Mullen, Michael D. ^{[1
]}

Zinsky, Amy H. ^{[1
]}

Rosario, Rose A. ^{[1
]}

Moura-Letts, Gustavo ^{[1
]}

机构：

[1] Rowan Univ, Dept Chem & Biochem, 201 Mullica Hill Rd, Glassboro, NJ 08028 USA

来源：

SYNLETT | 2024年 / 35卷 / 03期

基金：

美国国家科学基金会;

关键词：

photoisomerization; oxaziridines; nitrones; visible light; single-electron transfer; PHOTOREDOX CATALYSIS; PRIMARY AMINES; GAS-PHASE; AB-INITIO; OXAZIRIDINES; REARRANGEMENT; OXIDATION; CYCLOADDITION; NITRONES; AMINOHYDROXYLATION;

D O I：

10.1055/a-2153-6687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the first visible-light-promoted synthesis of vinyloxaziridines from simple conjugated nitrones. We have found that vinyl nitrones formed by the condensation reaction between conjugated carbonyls and hydroxylamines undergo visible-light-promoted energy transfer isomerization to the respective vinyloxaziridines in very high yields and selectivities. The reaction scope expands to a large array of substitution patterns, and evidence indicates that the proposed energy-transfer pathway is the predominant mechanism for this transformation.

引用

页码：325 / 329

页数：5

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