Synthesis 2007(1): 39-44  
DOI: 10.1055/s-2006-950376
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Approach to Substituted Dihydrofurans, Cyclopenta[b]furans and Tetrahydrobenzofurans

Shinji Tanimori*, Mitsunori Kirihata
Department of Bioscience and Informatics, Graduate School of Life and Environmental Science, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549918; e-Mail: tanimori@bioinfo.osakafu-u.ac.jp;
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Publikationsverlauf

Received 31 July 2006
Publikationsdatum:
21. November 2006 (online)

Abstract

The reaction of a symmetrical allylic dicarbonate or diacetate with a variety of β-keto esters in the presence of a palladium catalyst gave 2-substituted 5-vinyl-4,5-dihydrofuran-3-carboxylates, 4,6a-dihydro-3aH-cyclopenta[b]furan-3-carboxylates, and 3a,4,5,7a-tetrahydrobenzofuran-3-carboxylates in moderate to good yields.

11

According to our preliminary results, the corresponding chiral amides derived from either cyclic meso diacetate 3 or 5 with amide 8 were also separable on silica gel chromatography to afford diastereomerically pure (enantiomerically pure) dihydrofurans.