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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
Abstract : 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.
Keywords : Hydrocarbons Stereoselectivity Molecular structure Cations Salts
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02541577
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Submitted on : Tuesday, April 14, 2020 - 8:02:21 AM
Last modification on : Thursday, December 9, 2021 - 3:42:04 PM

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COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | CNRS | ENSICAEN | UNILEHAVRE | UNICAEN

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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, American Chemical Society, 2013, 15 (21), pp.5598-5601. ⟨10.1021/ol402837u⟩. ⟨hal-02541577⟩

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