One-Pot Synthesis of O-Allylhydroxylamines through the Organocatalytic Oxidation of Tertiary Allylic Amines Followed by a [2,3]-Meisenheimer Rearrangement

被引：28
|
作者：
Theodorou, Alexis [1 ]
Limnios, Dimitris [1 ]
Kokotos, Christoforos G. [1 ]
机构：
[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 13期
关键词：
alcohols; green chemistry; organocatalysis; oxidation; rearrangement; MEISENHEIMER REARRANGEMENT; N-OXIDES; ENANTIOSELECTIVE SYNTHESIS; CHIRALITY TRANSFER; AZETOPYRIDOINDOLES; DERIVATIVES; EPOXIDATION; ACID; 2,2,2-TRIFLUOROACETOPHENONE; 12-CARBAEUDISTOMIN;
D O I：
10.1002/chem.201406173
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A cheap, green, and highly efficient one-pot method for the synthesis of O-protected allylic alcohols is described. By utilizing 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, a variety of allylic amine N-oxides were synthesized, which upon heating are converted to the final products through a [2,3]-Meisenheimer rearrangement.
引用
收藏
页码：5238 / 5241
页数：4
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