Issue 23, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Asymmetric synthesis of tetrahydropyrans with competitive [1,2]-phenylsulfanyl (PhS) migrations

Lorenzo Caggiano,a   David J. Fox,b   David House,c   Zoe A. Jones,b   Fraser Kerrd  and  Stuart Warren*b  

* Corresponding authors

a Università degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, Via Venezian 21, 20133 Milano, Italy

b University Chemical Laboratory, Lensfield Road, Cambridge, UK
E-mail: sw134@cam.ac.uk

c Dyson Perrins Laboratory, South Parks Road, Oxford, UK

d AstraZeneca, Hurdsfield Industrial Estate, Macclesfield, Cheshire, UK

Abstract

Enantiomerically enriched triols were treated with trimethyl orthoacetate and pyridinium toluene-p-sulfonate to give a mixture of unrearranged THF and rearranged THP; treatment of the product mixture with toluene-p-sulfonic acid equilibrated the mixture to the THP.

Graphical abstract: Asymmetric synthesis of tetrahydropyrans with competitive [1,2]-phenylsulfanyl (PhS) migrations

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Article information

DOI
https://doi.org/10.1039/B208557G
Article type
Paper
Submitted
03 Sep 2002
Accepted
30 Sep 2002
First published
07 Nov 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2646-2651

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Asymmetric synthesis of tetrahydropyrans with competitive [1,2]-phenylsulfanyl (PhS) migrations

L. Caggiano, D. J. Fox, D. House, Z. A. Jones, F. Kerr and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2002, 2646 DOI: 10.1039/B208557G

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