Studies on the diastereoselectivity in the IMDA reactions of terminally activated ( E, E, E)-nona-1,6,8-trienes

The structure–diastereoselectivity relationships in the IMDA reactions of the terminally activated ( E, E, E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of...

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Bibliographic Details
Published in:Tetrahedron letters 2006-03, Vol.47 (10), p.1593-1598
Main Authors: Suzuki, Takahiro, Tanaka, Natsumi, Matsumura, Takehiko, Hosoya, Yosuke, Nakada, Masahisa
Format: Article
Language:English
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Summary:The structure–diastereoselectivity relationships in the IMDA reactions of the terminally activated ( E, E, E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3–C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.12.118