Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration

Jason Eames,*ab   David J. Fox,a   Maria A. de las Herasa  and  Stuart Warrena  

* Corresponding authors

a University Chemical Laboratory, Lensfield Road, Cambridge, UK

b Department of Chemistry, Queen Mary and Westfield College, Mile End Road, London, UK

Abstract

Single enantiomers and diastereoisomers of 2- and 3-alkyl-3-phenylsulfanyl-1,8-dioxa- and 1-oxa-8-thiaspiro[4.5]decanes can be prepared in good yield by acid-catalysed phenylsulfanyl (PhS-) migration. Either the syn- or anti-stereochemistry can be controlled by aldol reactions or by reduction of hydroxy-ketones.

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Article information

DOI
https://doi.org/10.1039/B001893G
Article type
Paper
Submitted
08 Mar 2000
Accepted
02 May 2000
First published
30 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1903-1914

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Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration

J. Eames, D. J. Fox, M. A. de las Heras and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2000, 1903 DOI: 10.1039/B001893G

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