Synlett 2013; 24(14): 1781-1784
DOI: 10.1055/s-0033-1339306
letter
© Georg Thieme Verlag Stuttgart · New York

Sequential Oxidation–Prins Reaction Processes Induced by the Same Iron Salt: Direct Access to 2-Aryl-4-Chloro-Tetrahydropyrans from Benzyl ­Alcohols

Fabienne Fache*
Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, ­Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France   Fax: +33(4)72448136   Email: piva@univ-lyon1.fr
,
Mickaël Muselli
Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, ­Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France   Fax: +33(4)72448136   Email: piva@univ-lyon1.fr
,
Olivier Piva*
Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, ­Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France   Fax: +33(4)72448136   Email: piva@univ-lyon1.fr
› Author Affiliations
Further Information

Publication History

Received: 03 May 2013

Accepted after revision: 03 June 2013

Publication Date:
18 July 2013 (online)


Abstract

A clay-supported iron(III) nitrate (Clayfen) was used as a stoichiometric reagent to first oxidize benzylic alcohols. The aldehydes thus obtained were converted in situ into tetrahydropyrans by way of a Prins cyclization induced by iron species already present in the media.

Supporting Information