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

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

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