Ln(OTf)3-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols

Daichi Nakamura; Yusuke Sasano; Yoshiharu Iwabuchi

doi:10.1039/C8OB02448K

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Ln(OTf)₃-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols†

Daichi Nakamura,

^a Yusuke Sasano

^a and Yoshiharu Iwabuchi

*^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan
E-mail: iwabuchi@mail.pharm.tohoku.ac.jp

Abstract

Regioselectivity of Ln(OTf)₃-catalysed alcoholysis of 2,3- and 3,4-epoxy alcohols was closely investigated to expand the scope of the transformations. The synthetic use was demonstrated by application to the construction of 4-propoxy-5-hydroxy-2,3-pentanedione (C4-propoxy-HPD), which is a potent synthetic mediator in AI-2 quorum sensing.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB02448K
Article type: Paper
Submitted: 01 Oct 2018
Accepted: 01 Mar 2019
First published: 02 Mar 2019

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Org. Biomol. Chem., 2019,17, 3581-3589

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Ln(OTf)₃-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols

D. Nakamura, Y. Sasano and Y. Iwabuchi, Org. Biomol. Chem., 2019, 17, 3581 DOI: 10.1039/C8OB02448K

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Organic & Biomolecular Chemistry