Issue 9, 2001
From the journal:

Chemical Communications

Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans

Eiman H. Al-Mutairi,a   Stuart R. Crosby,a   Julia Darzi,a   John R. Harding,b   Rachael A. Hughes,a   Clare D. King,b   Thomas J. Simpson,a   Robert W. Smitha  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

Cyclisation of homoallylic acetals under acidic conditions leads to the formation of 2,4,5-trisubstituted tetrahydropyrans with the creation of two new asymmetric centres with excellent stereocontrol. By varying the acid and the nucleophile, the reaction may be adapted for the preparation of 2,4,5-trisubstituted tetrahydropyrans with either a halide, alcohol, acetate or amide at C-4.

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Article information

DOI
https://doi.org/10.1039/B101414P
Article type
Communication
Submitted
13 Feb 2001
Accepted
12 Mar 2001
First published
11 Apr 2001

Chem. Commun., 2001, 835-836

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Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans

E. H. Al-Mutairi, S. R. Crosby, J. Darzi, J. R. Harding, R. A. Hughes, C. D. King, T. J. Simpson, R. W. Smith and C. L. Willis, Chem. Commun., 2001, 835 DOI: 10.1039/B101414P

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