A Straightforward and Highly Diastereoselective Access to Functionalized Monofluorinated Cyclopropanes via a Michael Initiated Ring Closure Reaction

Thibault Ferrary (1) , Emilie David (1) , Gaëlle Milanole (1) , Tatiana Besset (1) , Philippe Jubault (1) , Xavier Pannecoucke (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The synthesis of highly functionalized monofluorinated cyclopropanes based on a Michael Initiated Ring Closure (MIRC) reaction has been developed. The addition of quaternary ammonium salts derived from ethyl bromofluoroacetate on a panel of electron deficient alkenes followed by cyclization gave rise to an efficient access to monofluorinated cyclopropanes with good yields and remarkable diastereoselectivity.

Mots clés: Molecular structure; Stereoselectivity; Salts; Hydrocarbons; Cations

Domaines: Chimie

Thibault Ferrary, Emilie David, Gaëlle Milanole, Tatiana Besset, Philippe Jubault, et al.. A Straightforward and Highly Diastereoselective Access to Functionalized Monofluorinated Cyclopropanes via a Michael Initiated Ring Closure Reaction. Organic Letters, 2013, 15 (21), pp.5598-5601. ⟨10.1021/ol402837u⟩. ⟨hal-02541577⟩