title: Regio- and stereospecific synthesis of C-3 functionalized proline derivatives by palladium catalyzed directed C(sp3)-H arylation.
abstract: Functionalization of C(sp(3))-H bonds at the unactivated 3-position of proline derivatives has been achieved using aryl iodides and palladium catalysis. This directly affords cis-2,3-disubstituted pyrrolidines as single stereoisomers. 3-Arylation occurs in high yield under solvent-free conditions with aminoquinoline and methoxyaminoquinoline directing groups. The latter was readily removed to give primary amide derivatives with physicochemical properties appropriate for use as fragments in drug discovery.
authors.affiliation: Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, United Kingdom.
authors.forename: Dominic P
authors.initials: DP
authors.lastname: Affron
authors.forename: Owen A
authors.initials: OA
authors.lastname: Davis
authors.forename: James A
authors.initials: JA
authors.lastname: Bull
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006847:Hydrocarbons, Iodinated; D011759:Pyrrolidines; D010165:Palladium; D011392:Proline