Issue 17, 2007
From the journal:

Organic & Biomolecular Chemistry

Hosomi–Sakurai reactions of silacyclohexenes†

Nicholas J. Hughes,a   Robert D. C. Pullin,a   Mahesh J. Sanganee,b   Jonathan D. Sellars,a   Patrick. G. Steel*a  and  Michael J. Turnera  

* Corresponding authors

a Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
E-mail: p.g.steel@durham.ac.uk

b GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, UK

Abstract

Silacyclic allyl silanes, derived from silene–diene Diels–Alder reactions, combine with acetals in the presence of Lewis acids to afford, following oxidation of the intermediate fluorosilane, either butane-1,4-diols or tetrahydronaphthalenes containing four contiguous chiral centres with moderate to good diastereoselectivity.

Graphical abstract: Hosomi–Sakurai reactions of silacyclohexenes

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Article information

DOI
https://doi.org/10.1039/B709318G
Article type
Paper
Submitted
19 Jun 2007
Accepted
10 Jul 2007
First published
31 Jul 2007

Org. Biomol. Chem., 2007,5, 2841-2848

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Hosomi–Sakurai reactions of silacyclohexenes

N. J. Hughes, R. D. C. Pullin, M. J. Sanganee, J. D. Sellars, Patrick. G. Steel and M. J. Turner, Org. Biomol. Chem., 2007, 5, 2841 DOI: 10.1039/B709318G

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