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

页码：5238 / 5241

页数：4

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