title: Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones.
abstract: The transformation of a simple disubstituted pyridine into a pyridinium ion bearing an exocyclic hydroxyl group, protected as a silane, enabled an intramolecular hydride transfer reaction to take place when fluoride was used as a nucleophile. The addition was both regio- and stereoselective and enabled the formation of enantiopure dihydropyridones when enantiopure pyridine derivatives were used in this sequence. The heterocyclic products contain ample functionality for further elaboration reactions and subsequent derivatization.
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Connolly
authors.forename: Akshat H
authors.initials: AH
authors.lastname: Rathi
authors.forename: Lesley
authors.initials: L
authors.lastname: Walton
mesh_terms: D006865:Hydrogenation; D008958:Models, Molecular; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011726:Pyridinium Compounds; D011728:Pyridones