62779-69-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-1,2-Diamino-1-phenylethane is used as a chiral resolving agent for the production of enantiomerically pure pharmaceutical compounds. Its ability to selectively interact with other chiral molecules allows for the separation and purification of desired enantiomers, improving the efficacy and safety of pharmaceutical products.
Used in Chemical Synthesis:
(R)-(-)-1,2-Diamino-1-phenylethane is used as a chiral ligand, chiral auxiliary, and chiral building block in asymmetrical synthesis. Its unique structural properties enable the creation of complex chiral molecules with high selectivity and yield, facilitating the development of novel and efficient synthetic routes.
Used in Analytical Chemistry:
(R)-(-)-1,2-Diamino-1-phenylethane is used as a resolving reagent for the separation and identification of enantiomers in organic compounds. Its ability to form diastereomeric complexes with chiral analytes allows for the accurate determination of enantiomeric purity and composition in various chemical and biological systems.

Upstream product

• 5700-56-1 1,2-diaminophenylethane 
• 70-11-1 α-bromoacetophenone 
• 4589-97-3 phenylglyoxime 
• 53641-61-5 1-phenyl-1-acetylamino-2-acetylaminoethane 
• 94165-04-5 ethyl (S)-3-benzamido-3-phenylpropionate 
• 40639-03-0 (S)-3-benzoylamino-3-phenyl-propionic acid amide 
• 3082-69-7 ethyl (3S)-3-amino-3-phenylpropionate 
• 24461-61-8 (R)-Phenylglycine methyl ester 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 

Downstream Products

• 170242-71-4 (1R)-[N,N'-bis(2'-hydroxybenzylidene)]-1-phenyl-1,2-diaminoethane 
• 137766-76-8 (R)-2-phenylpiperazine 
• 84866-37-5 (R)-N¹,N²-Dimethyl-1-phenyl-ethane-1,2-diamine 
• 1609286-13-6 (R)-N,N'-(1-phenylethane-1,2-diyl)bis(2-chloroacetamide) 
• 1609286-17-0 (3R)-1-(chloromethyl)-3-phenyl-4-aza-1-azoniabicyclo[2.2.2]octane trifluoromethanesulfonate 
• 1609286-15-8 (3R)-1-(chloromethyl)-3-phenyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride 
• 1609286-14-7 (R)-2-phenyl-1,4-diazabicyclo[2.2.2]octane 
• 1280492-68-3 (R)-3-phenyl[1,2,5]thiadiazolidine-1,1-dioxide 
• 1017830-45-3 (R)-5-phenyl-2,3-piperazinedione 
• 95006-06-7 (R)-1.2-bis-benzamino-1-phenyl-ethane 
• 129867-64-7 (R)-1,2-Di(acetylamino)-1-phenylethane 

Relevant academic research and scientific papers

CHIRAL FLUORINATING REAGENTS

This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.

Asymmetric allylic substitution catalyzed by C1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction

Application of new chiral ligands (R)-(-)-12a and (S)-(+)-12c (VALDY), derived from amino acids, to the title reaction, involving cinnamyl (linear) and isocinnamyl (branched) type substrates (4 and 5 → 6), led to excellent regio- and enantioselectivities (>30:1, ≤98% ee), showing that ligands with a single chiral center are capable of high asymmetric induction. The structural requirements of the ligand and the mechanism are discussed. The application of single enantiomers of deuterium-labeled substrates (both linear 38c and branched 37c) and analysis of the products (41-43) by 2{ 1H) NMR spectroscopy in a chiral liquid crystal matrix allowed the stereochemical pathways of the reaction to be distinguished. With ligand (S)-(+)-12c, the matched enantiomer of branched substrate was found to be (S)-5, which was converted into (R)-6 with very high regio- and stereoselectivity via a process that involves net retention of stereochemistry. The mismatched enantiomer of the branched substrate was found to be (R)-5, which was also converted into (R)-6, that is, with apparent net inversion, but at a lower rate and with lower overall enantioselectivity. This latter feature, which may be termed a "memory effect", reduced the global enantioselectivity in the reaction of the racemic substrate (±)-5. The stereochemical pathway of the mismatched manifold has been shown also to be one of net retention, the apparent inversion occurring through equilibration via an Mo-allyl intermediate prior to nucleophilic attack. Incomplete equilibration leads to the memory effect and thus to lower enantioselectivity. Analysis of the mismatched manifold over the course of the reaction revealed that the memory effect is progressively attenuated with the nascent global selectivity increasing substantially as the reaction proceeds. The origin of this effect is suggested to be the depletion of CO sources in the reaction mixture, which attenuates turnover rate and thus facilitates greater equilibrium. The linear substrate was also converted into the branched product with net syn stereochemistry, as shown by isotopic labeling. An analogous process operates in the generation of small quantities of linear product from branched substrate.

Asymmetric molybdenum(0)-catalyzed allylic substitution

Application of new ligands (R)-(-)-8,(S)-(+)-16, and (S)-(+)-17 to the title reaction (1 or 2 → 3) led to excellent regio- and enantioselectivities (> 30:1; ≤ 98% ee); although lacking the C2-symmetry, the catalysts can be viewed as quasi-C2-symmetrical since the single chiral center is sufficient to determine the sense of wrapping of the metal by the ligand.

Synthesis of Chiral Atropoisomeric Square-planar Nickel(II) and Copper(II) Complexes formed by Macrocyclic Ligands containing Pendant Polyether Groups and a Quaternary Ammonium Group

Novel copper(II) and nickel(II) complexes of macrocyclic Schiff bases formed from derivatives of N,N'-bis(2-benzoylphenyl)oxamide and 1,2-diaminoethane have been prepared.In one case, separation of atropoisomeric chiral complexes has been achieved by preparative chromatography on SiO2.Quaternization of some of the complexes with an excess of MeI affords chiral complexes possessing a positively charged quaternary ammonium group and polyether podands in addition to a weakly electrophilic metal site.