Synthesis 2006(23): 3963-3966  
DOI: 10.1055/s-2006-950326
PAPER
© Georg Thieme Verlag Stuttgart · New York

Bismuth Triflate Catalyzed [1,3] Rearrangement of Aryl 3-Methylbut-2-enyl Ethers

Thierry Ollevier*, Topwe M. Mwene-Mbeja
Département de Chimie, Université Laval, Québec, PQ, G1K 7P4, Canada
Fax: +1(418)6567916; e-Mail: thierry.ollevier@chm.ulaval.ca;
Further Information

Publication History

Received 18 July 2006
Publication Date:
20 October 2006 (online)

Abstract

An efficient bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers has been developed. The reaction proceeds rapidly and affords the corresponding para- and ortho-prenylated phenols and naphthols in moderate to good yields (up to 86%). ortho-Prenylphenols are immediately cyclized under the reaction conditions to the corresponding chroman derivatives.