34585-11-0Relevant academic research and scientific papers
Efficient oxidative resolution of a P-stereogenic triarylphosphine and asymmetric synthesis of a P-stereogenic atropoisomeric biphenyl diphosphine dioxide
Dziuba, Kamil,Flis, Anna,Szmigielska, Anna,Pietrusiewicz, K. Michal
experimental part, p. 1401 - 1405 (2010/10/20)
Racemic 3-methoxyphenyl(1-naphthyl)phenylphosphine 1 was effectively resolved via an oxidative resolution procedure utilizing l-menthyl bromoacetate as the resolving agent to give enantiopure 3-methoxyphenyl(1-naphthyl) phenylphosphine oxide (R)-2 in 41% yield. Reduction of the resolved (R)-4 with HSiCl3/NEt3 provided the corresponding phosphine (R)-1 in >97% ee. Ortho-iodination of the enantiopure (R)-4 followed by Ullmann coupling of the resulting iodoarylphosphine oxide gave a P-stereogenic and atropoisomeric biphenyl diphosphine dioxide as a single diastereoisomer. The latter transformation constitutes the first example of an effective transfer of a P-centered chirality to an axial chirality of the atropoisomeric biaryl system. The absolute configurations of the resolved phosphine and the atropoisomeric biaryl system have also been established.
P-stereogenic phosphorus compounds: Effect of aryl substituents on the oxidation of arylmethylphenylphosphanes under asymmetric appel conditions
Rajendran, Kamalraj V.,Kennedy, Lorna,Gilheany, Declan G.
experimental part, p. 5642 - 5649 (2010/12/25)
The effects of aryl ring substitution on the dynamic resolution of aryl(methyl)phenylphosphanes under asymmetric Appel reaction conditions have been studied. As expected, substitution at the ortho position strongly affects the degree ofstereoselection tha
Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines
Peer, Markus,De Jong, Johannes C.,Kiefer, Matthias,Langer, Thomas,Rieck, Heiko,Schell, Heico,Sennhenn, Peter,Sprinz, Juergen,Steinhagen, Henning,Wiese, Burkhard,Helmchen, Guenter
, p. 7547 - 7583 (2007/10/03)
A series of enantiomerically pure 2-[2-(diarylphosphino)aryl]-oxazolines was prepared from commercially available or synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid (ii) ZnCl2 catalyzed condensation with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorous were prepared by either diastereoselective nucleophilic substitution of halogenide of Ar1Ar2PCl or by nucleophilic aromatic substitution with LiPAr1Ar2. In addition, sulfur and selenium analogs were prepared.
SYNTHESE DIRECTE DE PHOSPHINES TERTIARIES RACEMIQUES ET DE CHLOROPHOSPHINES DISSYMETRIQUES
Chodkiewicz, W.,Guillerm, D.,Jore, D.,Mathieu, E.,Wodzki, W.
, p. 107 - 114 (2007/10/02)
Racemic tertiary phosphines are obtained from dichlorophenylphosphine by a "one pot" synthesis in two steps: (1) condensation of one equivalent of an organocadmium, and (2) substitution of the second chlorine by another organometallic compound.The phosphines liberated from the resulting complexes can be stabilised by direct complexation with cuprous salts.The monochlorophosphines can be isolated in the first stage when their cadmium complexes are submitted to ligand exchange with pyridine.
