title: TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.
abstract: [reaction: see text] Two simple TADDOL-derived monodentate ligands, the (1R,2S)-2-phenylcyclohexanol-derived phosphite and the N,N-(phenylbenzyl)phosphoramidite, give comparably high levels of enantioselectivity (90-96% ee) in the rhodium-catalyzed hydroborations of substituted styrenes bearing either electron-donating or electron-withdrawing substituents. Rhodium(I) chloride and tetrafluoroborate catalyst precursors give comparable results. Pinacolborane is superior to catecholborane in these reactions.
authors.affiliation: Department of Chemistry and Nebraska Center for Materials and Nanoscience, University of Nebraska-Lincoln, 68588, USA.
authors.forename: Shin A
authors.initials: SA
authors.lastname: Moteki
authors.forename: Di
authors.initials: D
authors.lastname: Wu
authors.forename: Kusum L
authors.initials: KL
authors.lastname: Chandra
authors.forename: D Sahadeva
authors.initials: DS
authors.lastname: Reddy
authors.forename: James M
authors.initials: JM
authors.lastname: Takacs
mesh_terms: D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004148:Dioxolanes / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry
chemical_list: D001880:Boranes; D004148:Dioxolanes; D009943:Organophosphorus Compounds; D017905:Phosphites; D013343:Styrenes; C516101:alpha,alpha,alpha',alpha'-tetraaryl-1,3-dioxolane-4,5-dimethanol; C434331:phosphoramidite; D012238:Rhodium; D000432:Methanol