title: Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes.
abstract: A series of enantiopure 2,2'-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2'-bipyridines were found to be useful chiral ligands for the asymmetric aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-->84% ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-->86% ee).
authors.affiliation: School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
authors.forename: D R
authors.initials: DR
authors.lastname: Boyd
authors.forename: N D
authors.initials: ND
authors.lastname: Sharma
authors.forename: L
authors.initials: L
authors.lastname: Sbircea
authors.forename: D
authors.initials: D
authors.lastname: Murphy
authors.forename: J F
authors.initials: JF
authors.lastname: Malone
authors.forename: S L
authors.initials: SL
authors.lastname: James
authors.forename: C C R
authors.initials: CC
authors.lastname: Allen
authors.forename: J T G
authors.initials: JT
authors.lastname: Hamilton
mesh_terms: D015082:2,2'-Dipyridyl / Q000138:chemical synthesis / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D001711:Biotransformation; D004852:Epoxy Compounds / Q000737:chemistry; D008024:Ligands; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D016958:Pseudomonas putida / Q000201:enzymology; D011804:Quinolines / Q000378:metabolism*; D020578:Sphingomonas / Q000201:enzymology
chemical_list: D000447:Aldehydes; D004852:Epoxy Compounds; D008024:Ligands; D010087:Oxides; D011804:Quinolines; D015082:2,2'-Dipyridyl; C083774:2-chloroquinoline