Issue 22, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

Martin Christlieb,a   John E. Davies,a   Jason Eames,ab   Richard Hooleya  and  Stuart Warren*a  

* Corresponding authors

a University Chemical Laboratories, Lensfield Road, Cambridge, England
E-mail: sw134@cam.ac.uk

b Queen Mary, University of London, London, England

Abstract

A solution of 2-methyl-3-[1-(phenylsulfanyl)cyclohexyl]propane-1,3-diol 1 in toluene treated with triphenylphosphine, Ziram® 2 and DEAD, gave 3-methyl-2-[1-(phenylsulfanyl)cyclohexyl]oxetane 3 in 85% yield. A mechanistic study has been undertaken, optimal conditions have been found and the range of substrates for which the reaction is useful has been explored. We include the results of an X-ray study which shows that compound 33 (the oxidation product of diol 1) is a sulfone rather than a sulfoxide as previously reported.

Graphical abstract: The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

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Article information

DOI
https://doi.org/10.1039/B106851B
Article type
Paper
Submitted
01 Aug 2001
Accepted
27 Sep 2001
First published
30 Oct 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2983-2996

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The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

M. Christlieb, J. E. Davies, J. Eames, R. Hooley and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2001, 2983 DOI: 10.1039/B106851B

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