Synthesis of α-aminooxy amides through [3+3] cycloaddition and Sc(OTf)3-catalyzed double C-N bond cleavage in a one-pot reaction

被引：7

作者：

Luo, Yan ^{[1
]}

Chen, Chun-Hua ^{[1
]}

Zhu, Fan ^{[1
]}

Mo, Dong-Liang ^{[1
]}

机构：

[1] Guangxi Normal Univ, Minist Sci & Technol China, State Key Lab Chem & Mol Engn Med Resources, 15 Yu Cai Rd, Guilin 541004, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 40期

基金：

中国国家自然科学基金;

关键词：

AZA-OXYALLYL CATIONS; OXIME ETHER; CARBONYL-COMPOUNDS; VINYL NITRONES; TURN STRUCTURE; DERIVATIVES; PEPTIDES; HYDROXYLAMINES; AMINOXYLATION; BIOACTIVITY;

D O I：

10.1039/d0ob01788d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various alpha-aminooxy amides bearing a quaternary carbon at the alpha-position were prepared in good to excellent yields under mild reaction conditions fromN-vinyl nitrones and alpha-bromohydroxamates. TheN-vinyl nitrones tolerate a wide range ofN-vinyl fluorenone nitrones andN-vinyl isatin nitrones. Mechanistic studies show that the reaction initially proceeds through [3 + 3] cycloaddition betweenN-vinyl nitrones and aza-oxyallyl cations generated from alpha-bromohydroxamates to afford six-membered N,O-heterocycles, followed by double C-N bond cleavage in the presence of the Sc(OTf)(3)catalyst. A selective N-O bond cleavage of the obtained alpha-aminooxy amides is also realized under Fe/NH4Cl conditions. Furthermore, gram-scalable preparations of alpha-aminooxy amides are easily achieved.

引用

页码：8209 / 8218

页数：10

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