Issue 28, 2014
From the journal:

RSC Advances

One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols†

Julián Bergueiro,a   Javier Montenegro,*b   Carlos Saáb  and  Susana López*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultade de Química, Universidad de Santiago de Compostela, Santiago de Compostela, Spain
E-mail: susana.lopez.estevez@usc.es
Fax: +34 981 591 014

b Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, Santiago de Compostela, Spain
E-mail: javier.montenegro@usc.es

Abstract

Aluminium trichloride catalyses the expeditious direct conversion of tetrahydropyranyl ethers to silyl ethers. This one-step transformation is chemoselective versus deprotection of the acetal and hydrosilylation of unsaturated carbon–carbon bonds, and can also be applied to linear acetals. A possible mechanism is tentatively proposed.

Graphical abstract: One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

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Article information

DOI
https://doi.org/10.1039/C4RA00655K
Article type
Paper
Submitted
22 Jan 2014
Accepted
12 Mar 2014
First published
12 Mar 2014

RSC Adv., 2014,4, 14475-14479

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One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

J. Bergueiro, J. Montenegro, C. Saá and S. López, RSC Adv., 2014, 4, 14475 DOI: 10.1039/C4RA00655K

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