Issue 13, 2008
From the journal:

Chemical Communications

Intramolecular Prins cyclisations for the stereoselective synthesis of bicyclic tetrahydropyrans†

Jon D. Elswortha  and  Christine L. Willis*a  

* Corresponding authors

a School of Chemistry, University of Bristol, Bristol, UK
E-mail: chris.willis@bristol.ac.uk
Fax: +44 (0) 117 929 8611
Tel: +44 (0) 117 928 7660

Abstract

Methyl (4E,7R)-7-hydroxyoctanoate was prepared in 71% yield from ethyl (R)-3-hydroxybutanoate and on reaction with a series of aldehydes in the presence of TMSOTf gave bicyclic oxygen heterocycles in good yields and with the creation of three new stereogenic centres in a single pot.

Graphical abstract: Intramolecular Prins cyclisations for the stereoselective synthesis of bicyclic tetrahydropyrans

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Article information

DOI
https://doi.org/10.1039/B717078E
Article type
Communication
Submitted
05 Nov 2007
Accepted
21 Jan 2008
First published
21 Feb 2008

Chem. Commun., 2008, 1587-1589

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Intramolecular Prins cyclisations for the stereoselective synthesis of bicyclic tetrahydropyrans

J. D. Elsworth and C. L. Willis, Chem. Commun., 2008, 1587 DOI: 10.1039/B717078E

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