Synthesis of Spiroisoxazolines via TEMPO/NaNO2-Catalyzed Aerobic Oxidative Dearomatization

被引：9

作者：

Chen, Dengfeng ^{[1
]}

Wang, Yaming ^{[1
]}

Cai, Xu-Min ^{[1
]}

Cao, Xiaoji ^{[2
]}

Jiang, Ping ^{[1
]}

Wang, Fei ^{[1
]}

Huang, Shenlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn,Jiangsu Key Lab Biomass Based Gree, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Jiangsu Prov Key Lab Chem & Utilizat Agroforest B, Nanjing 210037, Peoples R China

[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 17期

关键词：

CATALYTIC ASYMMETRIC DEAROMATIZATION; BROMOTYROSINE ALKALOIDS; SPIROLACTONIZATION; CONSTRUCTION; METABOLITES; DERIVATIVES; CYCLIZATION; DIOXYGEN;

D O I：

10.1021/acs.orglett.0c02372

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic, aerobic oxidative dearomatization protocol has been developed for the preparation of spiroisoxazline scaffolds from oximes using TEMPO and NaNO2 as the catalyst and O-2 as the sole oxidant. This dearomatization methodology features its mild reaction conditions, good functional group tolerance, and an unprecedented broad substrate scope, encompassing phenols, aryl ethers, thiophenols, aryl sulfides, etc.

引用

页码：6847 / 6851

页数：5

共 57 条

[1] Bioactive brominated metabolites from the Red Sea sponge Suberea mollis [J].

Abou-Shoer, Mohamed I. ;

Shaala, Lamiaa A. ;

Youssef, Diaa T. A. ;

Badr, Jihan M. ;

Habib, Abdel-Azim M. .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (08) :1464-1467

[2] The synthesis of clavatadine C [J].

Badart, Michael P. ;

Squires, Chloe M. L. ;

Baird, Sarah K. ;

Hawkins, Bill C. .

TETRAHEDRON LETTERS, 2016, 57 (46) :5108-5111

[3] Reactive nitrogen species: Nitrosonium ions in organic synthesis [J].

Bering, Luis ;

Antonchick, Andrey P. .

TETRAHEDRON, 2019, 75 (09) :1131-1143

[4] Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon-heteroatom bond formation [J].

Bering, Luis ;

D'Ottavio, Laura ;

Sirvinskaite, Giedre ;

Antonchick, Andrey P. .

CHEMICAL COMMUNICATIONS, 2018, 54 (92) :13022-13025

[5] Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant [J].

Bering, Luis ;

Vogt, Melina ;

Paulussen, Felix M. ;

Antonchick, Andrey P. .

ORGANIC LETTERS, 2018, 20 (13) :4077-4080

[6] Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors [J].

Bering, Luis ;

Paulussen, Felix M. ;

Antonchick, Andrey P. .

ORGANIC LETTERS, 2018, 20 (07) :1978-1981

[7] Reversion of antibiotic resistance in Mycobacterium tuberculosis by spiroisoxazoline SMARt-420 [J].

Blondiaux, Nicolas ;

Moune, Martin ;

Desroses, Matthieu ;

Frita, Rosangela ;

Flipo, Marion ;

Mathys, Vanessa ;

Soetaert, Karine ;

Kiass, Mehdi ;

Delorme, Vincent ;

Djaout, Kamel ;

Trebosc, Vincent ;

Kemmer, Christian ;

Wintjens, Rene ;

Wohlkonig, Alexandre ;

Antoine, Rudy ;

Huot, Ludovic ;

Hot, David ;

Coscolla, Mireia ;

Feldmann, Julia ;

Gagneux, Sebastien ;

Locht, Camille ;

Brodin, Priscille ;

Gitzinger, Marc ;

Deprez, Benoit ;

Willand, Nicolas ;

Baulard, Alain R. .

SCIENCE, 2017, 355 (6330) :1206-1211

[8] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Hu, Wan-Ping ;

Munro, Murray H. G. ;

Northcote, Peter T. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2009, 26 (02) :170-244

[9] Synthesis of Spiroisoxazolines via an Oximation/Dearomatization Cascade under Air [J].

Chen, Dengfeng ;

He, Tianyu ;

Huang, Yuan ;

Luo, Jinyue ;

Wang, Fei ;

Huang, Shenlin .

ORGANIC LETTERS, 2020, 22 (11) :4429-4434

[10] Design, Synthesis, and Preliminary Studies of Spiro-isoxazoline-peroxides against Human Cytomegalovirus and Glioblastoma [J].

Das, Prasanta ;

Hasan, Mohammad H. ;

Mitra, Dipanwita ;

Bollavarapu, Ratna ;

Valente, Edward J. ;

Tandon, Ritesh ;

Raucher, Drazen ;

Hamme, Ashton T., II .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) :6992-7006

← 1 2 3 4 5 6 →