title: Iridium-N,P-ligand-catalyzed enantioselective hydrogenation of diphenylvinylphosphine oxides and vinylphosphonates.
abstract: Diphenylvinylphosphine oxides and di- and trisubstituted vinylphosphonates have been employed as substrates in iridium-catalyzed asymmetric hydrogenations. Complete conversions and excellent enantioselectivities (up to and above 99% ee) were observed for a range of substrates with both aromatic and aliphatic groups at the prochiral carbon. We have also hydrogenated electron-deficient carboxyethylvinylphosphonates with excellent stereoselectivity (up to and above 99% ee). The hydrogenated products of both classes of substrates are synthetically useful intermediates.
authors.affiliation: Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, 751 23 Uppsala, Sweden.
authors.forename: Pradeep
authors.initials: P
authors.lastname: Cheruku
authors.forename: Alexander
authors.initials: A
authors.lastname: Paptchikhine
authors.forename: Tamara L
authors.initials: TL
authors.lastname: Church
authors.forename: Pher G
authors.initials: PG
authors.lastname: Andersson
mesh_terms: D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D008024:Ligands; D009584:Nitrogen / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D008024:Ligands; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D010087:Oxides; D014753:Vinyl Compounds; C433467:vinylphosphonic acid; D010758:Phosphorus; D007495:Iridium; D009584:Nitrogen