Rhodium(I)-Catalyzed Intramolecular Hydroacylation of 4,6-Dienals: Novel Synthesis of Cycloheptenones

Yoshihiro Oonishi; Miwako Mori; Yoshihiro Sato

doi:10.1055/s-2007-983774

PAPER

Rhodium(I)-Catalyzed Intramolecular Hydroacylation of 4,6-Dienals: Novel Synthesis of Cycloheptenones

Yoshihiro Oonishi^a, Miwako Mori^b, Yoshihiro Sato*^a
^a Graduate School 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

Abstract

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Abstract

Rhodium(I)-catalyzed hydroacylation of 4,6-dienals was investigated. Hydroacylation of 4,6-dienals with a substituent at the C7 position produced cycloheptenone derivatives as the major products, while the cyclization of 4,6-dienals with no substituent at the terminus of the diene moiety preferentially gave cyclopentanone derivatives. The olefinic geometry of the diene moiety in 4,6-dienals also affected the reaction course, and the cyclization of substrates with an E-olefin at the C6 position produced cycloheptenone derivatives as the major products, while a cyclopentanone derivative was obtained from a substrate with a Z-olefin at the C6 position.

Key words

cyclization - dienals - hydroacylation - rhodium - transition metals

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