Synlett 2006(16): 2589-2592  
DOI: 10.1055/s-2006-950444
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Brønsted Acid Catalyzed Hosomi-Sakurai Reaction of Acetals

Daniela Kampen, Benjamin List*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062999; e-Mail: list@mpi-muelheim.mpg.de;
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Publikationsverlauf

Received 31 July 2006
Publikationsdatum:
22. September 2006 (online)

Abstract

Acetals react with allyltrimethylsilane in the presence of a catalytic amount of sulfonic acids to give the corresponding homoallylic ethers in high yields. The scope of the reaction is broad and both aromatic as well as aliphatic acetals can readily be used.

23

As suggested by a reviewer, the reaction may also be promoted by the in situ generated TMS sulfonate. For an example, see ref. 22a.