title: Sequential organocatalyzed Michael addition/[3 + 2]-heterocyclization for the stereoselective synthesis of fused-isoxazoline precursors of enantiopure cyclopentanoids.
abstract: We propose an asymmetric synthesis of functionalized cyclopentanoids bearing up to four stereogenic centers from easily accessible nitroalkenes and unsaturated aldehydes. The overall sequence includes an enantioselective organocatalytic Michael addition and a [3 + 2]-heterocyclization between an in situ generated silylnitronate and the unactivated double bond. Finally, the fused isoxazoline can be further transformed to various cyclopentanoids.
authors.affiliation: Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 CNRS UMR 6263, Centre Saint Jérôme, service 531, 13397 Marseille Cedex 20, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Bonne
authors.forename: Lydie
authors.initials: L
authors.lastname: Salat
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dulcère
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010422:Pentanones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007555:Isoxazoles; D010422:Pentanones