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

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

Organic letters (2013-10-22)
Thibault Ferrary, Emilie David, Gaëlle Milanole, Tatiana Besset, Philippe Jubault, Xavier Pannecoucke
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl bromofluoroacetate, 97%