Issue 13, 2016
From the journal:

Organic & Biomolecular Chemistry

Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines†

Nan Yan,‡a   Zheng Fang,‡a   Qing-Quan Liu,a   Xiao-Hong Guoa  and  Xiang-Guo Hu*a  

* Corresponding authors

a National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China
E-mail: huxiangg@iccas.ac.cn

Abstract

Utilizing molecular conformation as a controlling factor, epoxide-containing 2-aryl-piperidines can be ring-opened with the reagent combination of tetrabutylammonium fluoride (TBAF) and potassium bifluoride (KHF2) in a regioselective and divergent fashion. Four different types of hydroxylated fluoro-piperidines, valuable building blocks in drug development, were readily synthesized using this method. The basic nature of the reagent combination allowed a one-pot deprotection/ring opening process, which increased the efficacy of this transformation.

Graphical abstract: Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines

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Article information

DOI
https://doi.org/10.1039/C6OB00063K
Article type
Paper
Submitted
11 Jan 2016
Accepted
07 Mar 2016
First published
08 Mar 2016

Org. Biomol. Chem., 2016,14, 3469-3475

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Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines

N. Yan, Z. Fang, Q. Liu, X. Guo and X. Hu, Org. Biomol. Chem., 2016, 14, 3469 DOI: 10.1039/C6OB00063K

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