title: Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles.
abstract: The generation of cyclopent-2-enylzinc from cyclopentadiene based on a titanium-catalyzed hydroalumination/transmetallation sequence is described. Applied to the allylmetallation of phenylglycinol-derived imines, this sequence leads to homoallylic amines with moderate to good stereoselectivities. The synthesis of disubstituted azetidines and piperidines illustrates the potential of the method.
authors.affiliation: Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France. jean-luc.vasse@univ-reims.fr.
authors.forename: Michaël
authors.initials: M
authors.lastname: Coffinet
authors.affiliation: Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France. jean-luc.vasse@univ-reims.fr.
authors.forename: Samantha
authors.initials: S
authors.lastname: Lamy
authors.affiliation: Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France. jean-luc.vasse@univ-reims.fr.
authors.forename: Florian
authors.initials: F
authors.lastname: Jaroschik
authors.affiliation: Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France. jean-luc.vasse@univ-reims.fr.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Vasse