Novel stereoselective 1,2-rearrangement of Swaminathan ketone derivatives bearing a 7-membered ring under solvolysis conditions

[Display omitted] •Reported the novel rearrangement of Swaminathan ketone derivatives.•The rearrangement was proceeded under the simple solvolysis conditions.•Synthesis of Himachalane skeleton.•During the rearrangement, no significant loss of the optical purity was observed. A novel and stereoselect...

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Veröffentlicht in:Tetrahedron letters 2020-02, Vol.61 (9), p.151542, Article 151542
Hauptverfasser: Inomata, Kohei, Narita, Sanami
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •Reported the novel rearrangement of Swaminathan ketone derivatives.•The rearrangement was proceeded under the simple solvolysis conditions.•Synthesis of Himachalane skeleton.•During the rearrangement, no significant loss of the optical purity was observed. A novel and stereoselective 1,2-rearrangement of Swaminathan ketone derivatives bearing a 7-membered ring under solvolysis conditions afforded new bicyclic structures similar to the himachalane skeleton. During the reaction, there was no significant loss of optical purity, and the chirality of the starting material was preserved in the rearranged products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151542