title: Synthesis of Alkylidene(gem-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland-Claisen Rearrangement Sequence.
abstract: A one-pot difluorocyclopropenation/Ireland-Claisen rearrangement sequence applied to readily available propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of the unstable 3,3-difluorocyclopropenylcarbinyl glycolates arising from the difluorocyclopropenation. The Ireland-Claisen rearrangement proceeds with high diastereoselectivity and chirality transfer to afford alkylidene(gem-difluorocyclopropanes) incorporating a quaternary stereocenter and a protected glycolic acid moiety, which are useful building blocks for the preparation of functionalized gem-difluorocyclopropanes.
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI Paris, CNRS (UMR8231), PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Ernouf
authors.affiliation: Diverchim , 6 rue du Noyer, ZAC du Moulin, 95734 Roissy CDG, France.
authors.forename: Jean-Louis
authors.initials: JL
authors.lastname: Brayer
authors.affiliation: Diverchim , 6 rue du Noyer, ZAC du Moulin, 95734 Roissy CDG, France.
authors.forename: Benoît
authors.initials: B
authors.lastname: Folléas
authors.affiliation: Diverchim , 6 rue du Noyer, ZAC du Moulin, 95734 Roissy CDG, France.
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Demoute
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI Paris, CNRS (UMR8231), PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Christophe
authors.identifier: 0000-0003-3420-5584
authors.initials: C
authors.lastname: Meyer
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI Paris, CNRS (UMR8231), PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy