199396-00-4

Upstream product

• 90-11-9 1-Bromonaphthalene 
• 67-56-1 methanol 

Downstream Products

• 868948-35-0 P(C₆H₅)(C₁₀H₇)(CH(CH₃)2)BH₃ 
• 202756-07-8 (S)-P(BH₃)(Me)(Ph)(1-naphthyl) 
• 221277-78-7 (S,S)-1,1'-bis(1-naphthyl(phenyl)phosphino)ferrocene borane 
• 279243-51-5 (S)-(+)-1-naphthylphenylphosphinoferrocene 

Relevant academic research and scientific papers

About the Inversion Barriers of P-Chirogenic Triaryl-Substituted Phosphanes

The racemization tendency of acyclic P-chirogenic phosphanes is investigated experimentally and theoretically. Results of these investigations are important for the construction and use of P-chirogenic ligands and organocatalysts frequently used in asymmetric syntheses. Proof is given that triaryl phosphanes undergo easier racemization than compounds in which the phosphorus atom is linked to alkyl substituents. Interestingly, bulky ortho aryl substituents have only a marginal effect, whereas P-naphthyl rings destabilize the compound.

P-CHIRAL PHOSPHINE LIGANDS AND USE THEREOF FOR ASYMMETRIC SYNTHESIS

The present invention relates to chiral compounds with two optically active phosphorus atoms, chiral transition metal catalysts which comprise these compounds as ligands, a process for preparing the P-chiral compounds and processes for asymmetric synthesis using the chiral transition metal catalysts. The present invention specifically relates to a process for preparing an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of an optically active transition metal catalyst according to the invention. Yet more specifically, the present invention relates to a process for the asymmetric hydrogenation of citral, and also a process for preparing optically active menthol.

P-Chirogenic Xantphos Ligands and Related Ether Diphosphines: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation

A series of P-chirogenic Xantphos ligands and related diaryl ether diphosphines have been synthesized by a modification of the well-established Jugé method. The approach consists of the in situ deboranation of the chiral ephedrine-based phosphinite before the P-C coupling takes place. The stereochemical integrity of the stereocenters of the diphosphines during synthesis, long-time storage, and catalytic application was evaluated. In the rhodium-catalyzed asymmetric hydrogenation of isophorone as a model substrate for industrially relevant prostereogenic enones with some of the diphosphines, almost complete conversion, high chemoselectivity, and 96% ee were achieved.

Allylpalladium complexes with P-stereogenic monodentate phosphines. Application in the asymmetric hydrovinylation of styrene

A group of P-stereogenic monodentate phosphines S-PPhRR' (R = 1-naphthyl, 9-phenan-thryl, or o-biphenylyl and R' = CH3-, i-C3R 3-, and Ph3SiCH2-) have been prepared by succesive substitution reactions on the oxazaphospholidineborane obtained from (-)ephedrine and bis(N,N-diethylamino)phenylphosphine. The reaction with binuclear allyl compounds [Pd(μ-Cl)(allyl)]2 gives neutral [PdCl(allyl)P*] complexes. When allyl = 2-CH3-CsH4 (5), two isomers appeared in solution due to the R- or S-geometry around the palladium atom. The discrimination effect of the phosphines is small and the maximum isomeric ratio is observed for PPh(o-Ph2)(CH 2SiPh3). The molecular structure determined by X-ray diffraction of two complexes with P* = PPh(o-Ph2)(i-Pr) and PPh(o-Ph2)(OMe) showed a very similar nonsymmetric coordination of the allyl moiety according to the greater trans influence of the phosphorus atom. When allyl = 1-C6H5-C3H4 (6), the NMR spectroscopy showed up to four isomers due to the R- or S-geometry around palladium and the Z- or E-disposition of P* and the phenyl substituent of the allyl moiety. The E-isomers are the major species in solution, unique with PPh(o-Ph2)(CH2SiPh3). The usual, well-defined dynamic exchanges by π-σ-π and pseudorotation of the allyl moiety have been observed. The codimerization reaction between styrene and ethylene has been tested using filtered CH2Cl2 solutions of [PdCl(2-CH3-C3H4)P*] (5) complexes and AgBF4 as catalytic precursors. Moderate activity (TOF -1 at 25 °C) and good selectivities to 3-Ph-l-butene (-90% at 80% conversion) are obtained. The ee is moderate (a potentially secondary coordination atom occurs only when the substitution is in the phenyl ring and without significant improvements of the ee.