Issue 29, 2005
From the journal:

Chemical Communications

Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans

Conor S. Barry,a   Nick Bushby,b   John R. Harding,b   Rachael A. Hughes,a   Gregory D. Parker,a   Richard Roea  and  Christine L. Willis*a  

* Corresponding authors

a School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK
E-mail: chris.willis@bristol.ac.uk

b AstraZeneca UK Ltd., Mereside, Alderley Park, Macclesfield, UK

Abstract

Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

Graphical abstract: Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans

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Article information

DOI
https://doi.org/10.1039/B504562B
Article type
Communication
Submitted
01 Apr 2005
Accepted
19 May 2005
First published
16 Jun 2005

Chem. Commun., 2005, 3727-3729

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Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans

C. S. Barry, N. Bushby, J. R. Harding, R. A. Hughes, G. D. Parker, R. Roe and C. L. Willis, Chem. Commun., 2005, 3727 DOI: 10.1039/B504562B

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