Synthesis of á,á’- Di substituted Spiro[5, 5]-undecanes

Abstract

A spirane is an orthogonal structure where two rings share one common atom. The spirane framework is rigid, and as a consequence spiranes are potentially useful as rigid frameworks for attachment of coordination functions for metal complexation.

A spirane is an orthogonal structure where two rings share one common atom. The spirane framework is rigid, and as a consequence spiranes are potentially useful as rigid frameworks for attachment of coordination functions for metal complexation.

The goal for the project was 1) to synthesise I the dioxospiorne using ring closing methathesis (RCM), 2) for se if this reaction could provide I as a pure enantiomer, 3) to be triflated and substituents introduced via palladium- mediated coupling reactions. Stereoselective reduction was planned to furnish the cis,cis substituted functionalised spiranes II.