Synthesis of 6,6-disubstituted tetrahydrothiopheno [3,4-c] isoxazolines from beta-nitroenones

被引：5
|
作者：
Ahrach, M [1 ]
Schneider, R [1 ]
Gerardin, P [1 ]
Loubinoux, B [1 ]
机构：
[1] UNIV NANCY 1,FAC SCI,LAB CHIM ORGAN MICROBIOL,LERMAB,F-54506 VANDOEUVRE NANCY,FRANCE
来源：
SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 11期
关键词：
D O I：
10.1080/00397919708006787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta-Nitrosulfides 2, formed by Michael addition of prop-2-en-1-thiol to beta-nitroenones 1 in the presence of a catalytic amount of triethylamine, undergo either Intramolecular Nitrile Oxide Cycloadditions (INOC) or Intramolecular Silylnitronate Cycloadditions (ISOC) to functionalized 6,6-disubstituted tetrahydrothiopheno [3,4-c] isoxazolines 3 and 4. The stereoselectivity, poor by the INOC reactions starting from acyclic beta-nitroenones, is markedly increased with the ISOC procedure.
引用
收藏
页码：1865 / 1876
页数：12
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