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Synthesis 2009(6): 969-979  
DOI: 10.1055/s-0028-1087973
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium(I)-Catalyzed Cycloisomerization of 1,3-Dienes with Alkenes in a Tether

Yoshihiro Oonishia, Akira Saitoa, Miwako Morib, Yoshihiro Sato*a
a Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Fax: +81(11)7064982; e-Mail: biyo@pharm.hokudai.ac.jp;
b Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan
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Publikationsverlauf

Received 25 September 2008
Publikationsdatum:
24. Februar 2009 (online)

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Abstract

A rhodium(I)-catalyzed cycloisomerization of 1,3-dienes with alkenes in a tether proceeded smoothly, giving cyclopentene or cyclohexene derivatives in good yields. The existence of a hetero atom between the 1,3-diene moiety and the olefin in the tether affected the reaction course. In the case of the substrate having no hetero atom between the 1,3-diene moiety and olefin in the tether, cycloisomerization reaction proceeded, giving the corresponding cyclic product. On the other hand, in the case of the substrate having a hetero atom between the 1,3-diene moiety and olefin in the tether, the reaction course was completely changed to give a [4+2] cycloaddition product.

Key words

cyclizations - dienes - alkenes - rhodium - transition metals

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7

The [4+2] cycloaddition of 3b or 3i was independently reported by Livinghouse (3b and 3i) and Gilbertson(3b) (see ref. 5) with the formation of the same [4+2] adduct 5b or 5i. The spectral data of 5b and 5i obtained by us were identical with those reported.