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Article Dans Une Revue European Journal of Organic Chemistry Année : 2008

Stereoselective Synthesis of Bicyclo[4.2.1]nonanes: a Temporary-Bridge Approach to Cyclooctanoids

Résumé

A series of cis-α,γ-difunctionalized five-membered cyclic β- oxo esters have been chemo-, regio- and diastereoselectively prepared through an efficient domino anionic ring-cleavage/ ring-reconstitution/alkylation sequence including a 1,3-shift of the ester group. These unsaturated substrates were successfully engaged in various ring-closing metatheses to provide a reliable access to functionalized bicyclo[4.2.1]- nonanes, precursors of cyclooctanoids following the selective fragmentation of the one-carbon bridge.

Domaines

Chimie organique

Dates et versions

hal-00680577 , version 1 (19-03-2012)

Identifiants

Citer

Antoine Michaut, Sonia Miranda-Garcia, J. Carlos Menéndez, Yoann Coquerel, Jean Rodriguez. Stereoselective Synthesis of Bicyclo[4.2.1]nonanes: a Temporary-Bridge Approach to Cyclooctanoids. European Journal of Organic Chemistry, 2008, pp.4988-4998. ⟨10.1002/ejoc.200800702⟩. ⟨hal-00680577⟩
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