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Synthesis 2020; 52(18): 2721-2730
DOI: 10.1055/s-0040-1707889
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© Georg Thieme Verlag Stuttgart · New York

7-Siloxy-Substituted Hexahydronaphthalene Derivatives: Samarium Diiodide Promoted Synthesis and Typical Reactions

André Niermann
,
Hans-Ulrich Reissig  ∗
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
› Author AffiliationsThis work was supported by the Deutsche Forschungsgemeinschaft and Bayer HealthCare.
Further Information

Publication History

Received: 21 April 2020

Accepted after revision: 25 May 2020

Publication Date:
24 June 2020 (online)

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Dedicated to Professor Helmut Vorbrüggen on the occasion of his 90th birthday

Abstract

The samarium diiodide promoted reductive cyclization of a series of γ-aryl ketones with acetoxy, alkoxy, and siloxy groups in ortho-, meta-, and para-positions was investigated. Only precursors with p-acetoxy, p-tert-butoxy, or p-siloxy substituents furnished decent yields of the desired 7-oxy-1,2,3,4,6,8a-hexahydronaphthalene derivatives. The products were formed without contamination with the regio­isomeric bicyclic products containing conjugated double bonds. Typical reactions exploiting the silyl enol ether moiety of the 7-(tert-butyl­dimethylsiloxy)-1,2,3,4,6,8a-hexahydronaphthalene derivative were performed, allowing stereoselective access to highly substituted hexahydro­-, octahydro-, or decahydronaphthalene derivatives.

Key words

dearomatization - ketyl - hexahydronaphthalene - radical - samarium diiodide - silyl enol ether

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707889.
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