Sequential organocatalyzed Michael addition/[3 + 2]-heterocyclization for the stereoselective synthesis of fused-isoxazoline precursors of enantiopure cyclopentanoids.
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.
Bonne
Damien
D
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 CNRS UMR 6263, Centre Saint Jérôme, service 531, 13397 Marseille Cedex 20, France.
Salat
Lydie
L
Dulcère
Jean-Pierre
JP
Rodriguez
Jean
J
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
D007555:Isoxazoles; D010422:Pentanones