Asymmetric Synthesis of Polyfunctionalized Allenic Esters: Toward the Synthesis of an Iphionane Sesquiterpene

Aurélie Klein; Michel Miesch

doi:10.1055/s-2006-942463

PAPER

Asymmetric Synthesis of Polyfunctionalized Allenic Esters: Toward the Synthesis of an Iphionane Sesquiterpene

Aurélie Klein, Michel Miesch*
Laboratoire de Chimie Organique Synthétique (LCOS), Université Louis Pasteur - Institut de Chimie, LC 3 UMR 7177 CNRS/ULP 1, rue Blaise Pascal, 67008 Strasbourg, France
Fax: +33(3)90241754; e-Mail: miesch@chimie.u-strasbg.fr;

Abstract

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Abstract

Tetrabutylammonium fluoride (TBAF) reacts smoothly with optically active acetylenic ω-keto esters to afford optically active allenic esters (ee >95%) in high yield. After protection of the hydroxyl group, the addition of morpholine followed by an acidic hydrolysis, quantitatively led to optically active bicyclic α,β-unsaturated ketones (ee >95%). By using this methodology, the formal synthesis of an iphionane sesquiterpene was achieved.

Key words

alkynes - fluorine - domino reactions - nucleophilic addition - fused rings

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References

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