Organic Letters 2013-11-01

A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a Michael initiated ring closure reaction.

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

Index: Org. Lett. 15(21) , 5598-601, (2013)

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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.