221362-58-9Relevant academic research and scientific papers
Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
Poklukar, Ga?per,Stephan, Michel,Mohar, Barbara
supporting information, p. 2566 - 2570 (2018/05/16)
A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).
Ferrocenyl diphosphines containing stereogenic phosphorus atoms. Synthesis and application in the rhodium-catalyzed asymmetric hydrogenation
Maienza, Francesca
, p. 1041 - 1049 (2008/10/08)
Enantiomerically pure (R)-2-methoxyphenyl(phenyl)-O-methylphosphinite borane (1a) and CR)-1-naphthyl(phenyl)-O-methylphosphinite borane (1b) react with 1,1′-dilithioferrocene to give (S,S)-1,1′-bis(2-methoxyphenyl(phenyl)phosphino)ferrocene borane (2a) an
Nucleophilic displacement routes to P-chiral phosphines; the introduction of sterically encumbered groups
Brown, John M.,Laing, J. Christopher P.
, p. 435 - 444 (2007/10/03)
Methods for the asymmetric synthesis of P-chiral monophosphines carrying a bulky residue have been appraised. Reaction of 2-adamantylmagnesium bromide with P-chlorooxazaphospholidine 1 gives two diastereomeric products after oxidation with t-BuOOH; the SP isomer was characterised by X-ray and the RP isomer through a detailed NMR analysis. Although ring opening of either isomer 2 or 3 on reaction with o-anisylmagnesium bromide occurred satisfactorily, continuation of the desired reaction sequence through acid-catalysed methanolysis of the phosphinamide 4 and further with PhMgBr led to diminution of the enantiomeric purity in each step because of the more forcing conditions brought about by the steric demands of the 2-adamantyl residue. Similar difficulties were experienced when following the P-borane route of Juge and Genet, where the 2-adamantyl group was introduced in the initial step. More success was achieved by the borane route when the bulky residue was introduced last by reaction of RLi with the phosphinite complex 13. In this way the ferrocenyl, 1-adamantyl and t-butylphosphines carrying both phenyl and o-anisyl residues, were formed as borane complexes. Deboronation proceeded smoothly in the first two cases to give the tertiary phosphines in greater than 92% e.e.
