Construction of novel spiroisoxazolines via intramolecular cyclization/methylation

被引：11

作者：

Ellis, Erick D. ^{[1
]}

Xu, Jianping ^{[1
]}

Valente, Edward J. ^{[2
]}

Hamme, Ashton T., II ^{[1
]}

机构：

[1] Jackson State Univ, Dept Chem & Biochem, Coll Sci Engn & Technol, Jackson, MS 39217 USA

[2] Univ Portland, Dept Chem, Portland, OR 97203 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 39期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

Intramolecular cyclization; Cycloaddition; Regioselectivity; Spirocycles; Heterocycles; 1,3-DIPOLAR CYCLOADDITION REACTION; MARINE SPONGE METABOLITES; OXIDATIVE CYCLIZATION; AEROTHIONIN; ALKALOIDS; ISOXAZOLINES; VERONGAMINE; REACTIVITY; ACCESS;

D O I：

10.1016/j.tetlet.2009.07.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Improved yields for the syntheses of a variety of spiroisoxazolines were achieved through intramolecular cyclization/methylation reactions of functionalized 5,5-disubstituted isoxazolines in one reaction vessel. Aromatic ring containing nitrile oxides and disubstituted geminal alkenes reacted in a 1,3-dipolar fashion to afford the corresponding 5,5-isoxazoline. A comparison of the relative location of the nucleophile and electrophile on the isoxazoline and two different ester functional groups was performed in order to determine the best isoxazoline system for the intramolecular cyclization/methylation reaction. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5516 / 5519

页数：4

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