title: Diastereoselective three-component vinylogous Mannich reaction of nitrogen heterocycles, acyl/sulfonyl chlorides, and silyloxyfurans/pyrroles.
abstract: A one-step, 3-component vinylogous Mannich reaction of trimethylsilyloxyfuran or N-protected tert-butyldimethylsilyloxypyrrole with a variety of nitrogen-containing heterocycles in the presence of diverse electrophiles is described. The reaction products were generally obtained in high yields and as a single diastereoisomer having the (R*,R*) relative configuration based on crystallographic studies of several derivatives. Several azaheterocycles were successfully used for this reaction, such as isoquinolines, quinoline, phenanthridine, quinazoline, phthalazine, and β-carboline, and electrophiles included acetyl chloride, methyl chloroformate, methyl chloromalonate, 2-bromobutanoyl chloride, and arylsulfonyl chlorides. The products of the vinylogous Mannich reactions were subjected to further transformations, leading to highly functionalized and stereochemically defined tetracyclic derivatives that are valuable building blocks for the preparation of natural products or medicinal agents.
authors.affiliation: Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles , UPR 2301, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Simon
authors.initials: S
authors.lastname: Janody
authors.forename: Philippe
authors.initials: P
authors.lastname: Hermange
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Josiane
authors.initials: J
authors.lastname: Thierry
authors.forename: Robert H
authors.initials: RH
authors.lastname: Dodd
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*
chemical_list: C454640:2-trimethylsilyloxyfuran; D005663:Furans; D006571:Heterocyclic Compounds; D013441:Sulfinic Acids; C044255:sulfonyl chloride; D009584:Nitrogen