title: Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams.
abstract: N-aryl γ-lactams react intermolecularly with acceptor-acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a Lewis acid, subsequent Friedel-Crafts reactions yield tricyclic pyrrolizidines in excellent yields (90-96 %) and diastereoselectivities (up to >20:1).
authors.affiliation: Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Goudedranche
authors.affiliation: Laboratoire de Cristallographie, Université de Genève, quai Ernest Ansermet 24, 1211, Geneva 4, Switzerland.
authors.forename: Céline
authors.initials: C
authors.lastname: Besnard
authors.affiliation: Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
authors.forename: Léo
authors.initials: L
authors.lastname: Egger
authors.affiliation: Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland. jerome.lacour@unige.ch.
authors.forename: Jérôme
authors.identifier: 0000-0001-6247-8059
authors.initials: J
authors.lastname: Lacour
keywords: acyl migrations; diazo reagents; pyrrolidines; pyrrolizidines; γ-lactams