title: Highly diastereoselective three-component vinylogous Mannich reaction between isoquinolines, acyl/sulfonyl chlorides, and silyloxyfurans.
abstract: Reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride provides easy access to a wide variety of isoquinolinobutyrolactones with excellent yields and diastereoselectivites (R*,R* isomer), even in the case of formation of quaternary centers (i.e., R(3) or R(4) = Me). Moreover, the use of a chiral auxiliary allowed formation of a single stereoisomer in 96% yield. This represents the first examples of asymmetric vinylogous Mannich reactions on isoquinolinium salts.
authors.affiliation: Institut de Chimie des Substances Naturelles - CNRS UPR 2301, Gif-sur-Yvette, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Hermange
authors.forename: Marie Elise
authors.initials: ME
authors.lastname: Tran Huu Dau
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Robert H
authors.initials: RH
authors.lastname: Dodd
mesh_terms: D002384:Catalysis; D007536:Isomerism; D007546:Isoquinolines / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*
chemical_list: D007546:Isoquinolines; D013441:Sulfinic Acids; C044255:sulfonyl chloride