title: Stereoselective preparation of β,γ-methano-GABA derivatives.
abstract: The Kulinkovich-de Meijere reaction between an unsaturated Grignard reagent and a chiral amide takes place with a high trans stereoselectivity and provides a convenient access to non-racemic trans cyclopropylamines. These compounds are transformed in four steps into the corresponding N-protected β,γ-methano-GABA derivatives, which are obtained for the first time in enantiomerically pure form. The corresponding transformations of the cis cyclopropylamine adducts are also described.
authors.affiliation: Laboratoire de Synthèse Organique et Méthodologie, ICMMO (UMR 8182 CNRS), Bât. 420, Université Paris-Sud 11, 15 rue Georges Clemenceau, 91405, Orsay, France. david.aitken@u-psud.fr
authors.forename: David J
authors.initials: DJ
authors.lastname: Aitken
authors.forename: Ludovic
authors.initials: L
authors.lastname: Drouin
authors.forename: Sarah
authors.initials: S
authors.lastname: Goretta
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.forename: Jean
authors.initials: J
authors.lastname: Ollivier
authors.forename: Marco
authors.initials: M
authors.lastname: Spiga
mesh_terms: D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003521:Cyclopropanes; D005680:gamma-Aminobutyric Acid; C067351:cyclopropylamine