154675-31-7

Upstream product

• 942066-05-9 N-[(1E)-1-phenylpropylidene]-P,P-diphenylphosphinic amide 
• 98837-46-8 P,P-diphenyl-N-(phenylmethylene)phosphinic amide 
• 557-20-0 diethylzinc 
• 93-54-9 1-Phenyl-1-propanol 
• 5994-87-6 diphenylphosphinamide 
• 17157-61-8 bis(diphenylphosphino)amine 
• 23517-42-2 propiophenone oxime 
• 2157-50-8 propiophenone oxime 
• 93-55-0 1-phenyl-propan-1-one 
• 106651-13-2 P,P-diphenyl-N-(1-phenylpropylidene)phosphinic amide 
• 2386-64-3 ethylmagnesium chloride 
• 98837-46-8 N-benzylidenediphenylphosphinamide 

Downstream Products

• 3789-59-1 (R)-1-phenylpropylamine 
• 2941-20-0 1-phenylpropylamine 

Relevant academic research and scientific papers

Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex

Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.

A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation

This manuscript describes a modular method for preparing N-alkyl phosphinic amides from primary or secondary alcohols and primary phosphinic amide (R1R2P = ONH2) nucleophiles via transfer hydrogenation. The transformation typically proceeds in excellent yields, employs conveniently available reagents, and produces water as the only byproduct.

Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes

A series of zinc acetate complexes with optically pure diphenylethanediamine (DPEDA)-derived ligands have been employed as enantioselective catalyst for the hydrosilylation of various imines. High control of stereoselectivity (up to 97% ee) and excellent yields (up to 96%) were gained for a broad range of N-phosphinoylimines by using (R,R)-N,N′-dibenzyl-1,2-diphenylethane-1,2-diamine. This is the first successful application of an air-stable and environmentally friendly chiral Zn(OAc)2 complex instead of the previously used harmful diethylzinc in the asymmetric reduction of the C=N double bond.

Enantioselective addition of dialkylzinc to aromatic aldimines mediated by camphor-derived chiral β-amino alcohols

The enantioselective addition of diethylzinc or dimethylzinc to N-(diphenylphosphinoyl)imines mediated by 1 or 2 could be achieved in high yields (70-97%) and enantioselectivities (85-98% ee). The catalytic loading of 1 or 2a could be reduced to 10 mol% f

METHODS FOR PREPARING DIORGANOZINC COMPOUNDS

There are provided methods for preparing the diorganozmc compounds of formula R2Zn (I or Ia), where R is a defined organic radical, and the two R groups can be the same or different The starting material is the zinc compound ZnX2 (II) or R2ZnX (IIa), where X is a defined anion and R2 is a defined organic radical. The zinc reagent of type II is combined with a Grignard reagent and also, when X is Cl or Br, with an alkali metal reagent (VI) to form the diorganozinc product (I or Ia). Also provided are methods for preparing the zinc alcoholates of formula Zn(OR1)2 by reaction of ZnX2, where X = Cl or Br, with an alkali metal reagent of the formula MOR1, where M = Na or K, and where R1 is a defined organic radical.

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines

(Chemical Equation Presented) Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd-(CF3CO 2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.

Nickel-catalysed addition of dialkylzinc reagents to N-phosphinoyl- and N-sulfonylimines

A catalytic amount of a nickel complex (0.1-5.3 mol %) extraordinarily increases the reaction rate of the addition of dialkylzinc reagents to N-(diphenylphosphinoyl)- or N-(benzenesulfonyl)imines. The reaction of imines derived from both aromatic and alip

Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing cinchonidine and cinchonine as chiral ligands

The use of the 'pseudoenantiomeric pair' of cinchonine and cinchonidine as ligands for the addition of diethylzinc to N-diphenylphosphinoylimines has been investigated. With 1equiv of cinchonidine as ligand, a series of chiral amines was prepared in good

Evidence for the structure of the enantioactive ligand in the phosphine-copper-catalyzed addition of diorganozinc reagents to imines

(Chemical equation presented). Mistaken identity: The active catalyst in the highly selective Cu-catalyzed nucleophilic addition of diorganozinc reagents to N-diphenylphosphinoylimines (see scheme) does not contain the bis(phosphine) ligand 1 but rather t

Camphorsulfonamide derivatives: A new class of chiral catalysts for the titanium alkoxide-promoted addition of dialkylzinc to aldehydes

The enantioselective addition of dialkylzinc to several aldehydes, using different chiral bidentate ligands (3a-j, 4a-h) [derived from (+)-10-camphorsulfonyl chloride] and titanium alkoxide as catalysts, is studied. The influence of temperature, titanium alkoxide, stoichiometry, additive, aldehyde and ligand structure is also studied.