title: Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites.
abstract: A new generation of monodentate phosphoramidite ligands bearing a primary amine moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl alpha-acetoxyacrylate or (E)-beta-aryl itaconate derivatives, affording the corresponding hydrogenation products with excellent enantioselectivities (up to >99% ee). The presence of intermolecular hydrogen bonding (HB) between two monodentate ligands in the catalyst was found to be critical for excellent catalyst performance. This finding provides a basis for design and development of further catalyst systems using this type of monodentate phosphoramidite ligands.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PR China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Christian A
authors.initials: CA
authors.lastname: Sandoval
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Yamaguchi
authors.forename: Xue
authors.initials: X
authors.lastname: Zhang
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Koichi
authors.initials: K
authors.lastname: Kato
authors.forename: Kuiling
authors.initials: K
authors.lastname: Ding
mesh_terms: D002384:Catalysis; D006860:Hydrogen Bonding; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D008024:Ligands; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D012238:Rhodium