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Synlett 2005(18): 2808-2810  
DOI: 10.1055/s-2005-918916
LETTER
© Georg Thieme Verlag Stuttgart · New York

Selective Tetrahydropyranylation under Non-Acidic Conditions

Rabah Azzouza, Laurent Bischoff*a, Marc-Henri Fouquetb, Francis Marsaisa
a Laboratoire de Chimie Organique Fine et Hétérocyclique, IRCOF-INSA Rouen, B.P. 08, 76131 Mont-Saint-Aignan, France
b I.U.T. Rouen, Rue Lavoisier, 76821 Mont-Saint-Aignan, France
Fax: +33(2)35522962; e-Mail: laurent.bischoff@insa-rouen.fr;
Further Information

Publication History

Received 30 June 2005
Publication Date:
10 October 2005 (online)

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Abstract

We report that the tetrahydropyranylation of hydroxyl groups, exhibiting especially very low nucleophilicities, can be achieved by means of Mitsunobu reaction with 2-hydroxytetra­hydropyran. This reaction led to the protection of phenols and ­pyridinols without the use of an acidic catalyst. For instance ­hydroxypyridines could not be protected by dihydropyran under acidic conditions, whereas they underwent a smooth tetrahydro­pyranylation under Mitsunobu conditions. The method is selective for a phenol over an alcohol.

Key words

protecting groups - glycosylations - acetals - phenols - pyridines

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