Ring expansion induced by DAST:: Synthesis of substituted 3-fluoropiperidines from prolinols and 3-fluoroazepanes from 2-hydroxymethylpiperidines

被引：48

作者：

Dechamps, Ingrid ^{[1
]}

Pardo, Domingo Gomez ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] Ecole Super Phys & Chim Ind Ville Paris, CNRS, Lab Chim Organ Assoc, F-75231 Paris, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 25期

关键词：

ring expansion; rearrangement; fluorine; aziridinium; nitrogen heterocycles;

D O I：

10.1002/ejoc.200700237

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Optically active prolinols can be converted into optically active 3-fluoropiperidines by treatment with DAST. The reaction often produces 2-fluoromethylpyrrolidines as byproducts. The ring expansion was also applied to 2-hydroxypiperidines to produce 3-fluoroazepanes. The rearrangement proceeds via an aziridinium intermediate. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：4224 / 4234

页数：11

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