36617-88-6Relevant articles and documents
Nickel-catalyzed asymmetric hydrovinylation using lewis acid activation
Lassauque, Nicolas,Francio, Giancarlo,Leitner, Walter
, p. 3199 - 3202 (2009)
A broad range of commercially available Lewis acids were investigated for their ability to activate and regulate nickel catalysts for asymmetric hydrovinylation processes using styrene as model substrate and ligand (R a,Sc,Sc/s
Phosphoramidite quinaphos-type ligands for highly selective Ni-catalysed asymmetric C-C bond forming reactions
Diez-Holz, Christiane J.,Boeing, Christian,Francio, Giancarlo,Hoelscher, Markus,Leitner, Walter
, p. 2995 - 3002 (2007)
Monodentate quinaphos phosphoramidites bearing different substituents in the 2-position of the 1,2-dihydroquinoline backbone were synthesised and characterised. Computational, NMR spectroscopic and X-ray crystallographic methods were used for the elucidat
ASYMMETRISCHE KATALYSEN. VI. NiCl2(-)NORPHOS-KATALYSIERTE CROSS-COUPLING-REAKTION VON 1-PHENYLETHYL-GRIGNARD MIT VINYLBROMID
Brunner, H.,Proebster, M.
, p. C1 - C3 (1981)
In the cross-coupling of racemic 1-phenylethyl-Grignard with vinylbromide catalyzed by NiCl2(-)Norphos, (S)-3-phenyl-1-butene is obtained in 95percent chemical yield and 67percent optical yield.
P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
Xiong, Wenrui,Xu, Guangqing,Yu, Xinhong,Tang, Wenjun
, p. 4003 - 4013 (2019/06/24)
Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.
Neutral and Cationic Palladium Complexes of P-Stereogenic Phosphanes Bearing a Heterocyclic Substituent
Clavero, Pau,Grabulosa, Arnald,Rocamora, Mercè,Muller, Guillermo,Font-Bardia, Mercè
, p. 4216 - 4225 (2016/09/16)
The coordination chemistry of 13 optically pure P-stereogenic diarylmonophosphanes P(Het)PhR [Het = 4-dibenzofuranyl (DBF), 4-dibenzothiophenyl (DBT), 4-dibenzothiophenyl S,S-dioxide (DBTO2) and 1-thianthrenyl (TA); R = OMe, Me, iPr, Fc (ferroc
Synthesis of P-Stereogenic Phosphoramidite and Phosphorodiamidite Ligands and Their Application in Asymmetric Catalysis
Schmitz, Christian,Leitner, Walter,Franciò, Giancarlo
, p. 6205 - 6230 (2015/10/06)
A series of P-stereogenic monodentate phosphoramidite (PNO2) and phosphorodiamidite (PN2O) ligands based on chiral Betti bases has been prepared by modular synthetic procedures. The chirality at the phosphorus can be controlled to a large extent by the synthetic route, leading to stereoselective access to single P-epimers. The absolute configuration of the P-atom was assigned by X-ray diffraction analysis. The new ligands were evaluated in asymmetric catalysis and the influence of the exocyclic amine or alcohol moiety as well as the interplay between the P-chirality and the stereocenters in the backbone were investigated. Enantioselectivities of up to 85 and 83 % ee were obtained in the Rh-catalyzed hydrogenation of dimethyl itaconate and in the Pd-catalyzed allylic amination of (rac)-(E)-1,3-diphenylallyl acetate with benzylamine, respectively. In the Ni-catalyzed hydrovinylation of styrene, ee values of up to 68 %, excellent chemoselectivities, and high activities (TOFav up to 3000 h-1) were achieved. A series of phosphoramidite (R = OR) and phosphorodiamidite (R = NR2) ligands containing a stereogenic phosphorus atom has been synthesized from chiral Betti bases as amino alcohol building blocks. The new ligands have been applied in three different asymmetric metal-catalyzed reactions, and the interplay between P-stereochemistry, structural features of R, and chirality at the backbone evaluated.
