1008-63-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-AMINO-2-PHENYL-PROPIONIC ACID is used as a precursor for the synthesis of various pharmaceutical compounds, including neurotransmitters such as dopamine, norepinephrine, and epinephrine. These neurotransmitters play a crucial role in regulating mood, attention, and other cognitive functions.
Used in Food and Beverage Industry:
(R)-3-AMINO-2-PHENYL-PROPIONIC ACID is used as a flavor enhancer and a building block for protein synthesis in the food and beverage industry. Its presence in various food sources contributes to the overall protein content and amino acid profile, which is essential for maintaining good health.
Used in Nutraceutical Industry:
(R)-3-AMINO-2-PHENYL-PROPIONIC ACID is used as a dietary supplement in the nutraceutical industry to support protein synthesis and overall health. It can be particularly beneficial for individuals with phenylketonuria (PKU), a genetic disorder that results in an inability to metabolize phenylalanine, as it helps maintain appropriate levels of this essential amino acid in the body.
Used in Sweetener Production:
(R)-3-AMINO-2-PHENYL-PROPIONIC ACID is used as a key ingredient in the production of the artificial sweetener aspartame. Aspartame is a low-calorie sweetener that is widely used in various food and beverage products, offering a sweet taste without the added calories of sugar.

Upstream product

• 50-00-0 formaldehyd 
• 2613-89-0 phenylmalonic acid 
• 131081-27-1 2-phenyl-3-phthalimido-propionitrile 
• 102449-74-1 (benzoylamino-methyl)-phenyl-malonic acid diethyl ester 
• 712-57-2 (+/-)-2-phenyl-succinamic acid 
• 112864-34-3 phenyl-phthalimidomethyl-malonic acid diethyl ester 
• 135959-07-8 α-(aminomethyl)benzeneacetic acid,ethyl ester 
• 91012-17-8 (+/-)-methyl 3-amino-2-phenylpropanoate hydrochloride 
• 7647-01-0 hydrogenchloride 
• 24331-94-0 1,4-dihydro-3(2H)-isoquinolinone 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 492-38-6 2-phenylacrylic acid 
• 7803-49-8 hydroxylamine 

Downstream Products

• 58521-53-2 C₁₅H₂₇NO₂Si₂ 
• 1235987-04-8 C₁₀H₁₄N₂O 
• 99092-02-1 methyl 3-amino-2-phenylpropanoate 

Relevant academic research and scientific papers

Enantiopure N-Benzyloxycarbonyl-β2-amino Acid Allyl Esters from Racemic β-Lactams by Dynamic Kinetic Resolution using Candida antarctica Lipase B

The dynamic kinetic resolution of α-substituted racemic β-lactams by alcoholytic ring-opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic α-substituted N-Cbz-azetidinones (Cbz=benzyloxycarbonyl) was transformed to the corresponding N-Cbz-protected β2-amino acid allyl esters with high enantioselectivity (up to 99%) and high yields (up to quantitative) at room temperature.

Pd-catalyzed asymmetric conjugate addition of arylboronic acids to 2-nitroacrylates: A facile route to β2-homophenylglycines

Asymmetric conjugate addition of arylboronic acids to 2-nitroacrylamide in the presence of cationic palladium-Chiraphos complex proceeds with high yield and enantioselectivity (73-89% ee) using as low as 0.05-0.25 mol % of the catalyst. The adducts can be smoothly transformed into the corresponding β2-homophenylglycines in two simple steps.

Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

(R)-(+)-3-Amino-2-phenylpropanoic Acid: a Revised Absolute Configuration based on an Enantioselective Synthesis and an X-Ray Crystal Structure of the Salt with (1S)-(+)-Camphor-10-sulfonic Acid

Amidoalkylation of the lithium enolate of (4S,5R)-4-methyl-5-phenyl-3-(phenylacetyl)oxazolidin-2-one 5 by 1-(N-benzyloxycarbonylaminomethyl)benzotriazole 2c, followed by cleavage of the oxazolidinone chiral auxiliary and of the N-benzyloxycarbonyl group, gave (R)-(+)-3-amino-2-phenylpropanoic acid 1, the absolute configuration of which was determined by X-ray crystallography on the salt 8 with (1S)-(+)-camphor-10-sulfonic acid.

(S)-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) acetic acid as a solid supported chiral auxiliary in the asymmetric synthesis of β2-homoarylglycines

Diastereoselective additions of the resin-supported (S)-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) acetic acid to phthalimidomethyl aryl ketenes allow solid phase preparation of β2-homoarylglycines with reasonable degrees of stereoselectivity.

Novel asymmetric catalytic nucleophilic fluorine heterocyclization reaction system and application thereof in chiral non-natural amino acid module synthesis

The invention discloses a novel asymmetric catalytic fluorine heterocyclization reaction system and application thereof. The novel asymmetric catalytic fluorine heterocyclization reaction system provided by the invention comprises a chiral iodine catalyst and etherified boron trifluoride, and is applied to a catalytic asymmetric nucleophilic fluorine heterocyclization reaction of unsaturated amide; a fluoro oxazine derivative is obtained through treatment after the reaction; and the obtained fluoro oxazine derivative is subjected to hydrolysis and oxidation reaction to obtain the chiral non-natural amino acid. The reaction system provided by the invention has the following advantages: etherified boron trifluoride is used as a fluorine reagent, is cheap and easy to obtain, and has good stability and low toxicity; the reaction conditions are mild; the chiral iodine catalyst is simple to prepare and does not need a complex ligand; the system is environment-friendly and free of heavy metal pollution and precious metal waste; the obtained product is a fluoro oxazine derivative active molecular structure unit with two chiral centers; chiral non-natural amino acid can be obtained through conversion reaction of the product; and the chemical selectivity and stereoselectivity of the reaction are good, and the yield and optical purity are high.

Asymmetric Synthesis of β2-Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki–Miyaura Arylation of Aziridine-2-carboxylates

A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki–Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched β2-aryl amino acids, starting from co

Organocatalytic enantioselective Michael addition of a kojic acid derivative to nitro olefins

By employing a chiral bifunctional thiourea-tertiary amine as catalyst, enantioselective Michael addition of a kojic acid derivative to nitro olefins was realised. The reactions afforded the products with good yields (up to 99%) in good enantioselectivities (up to 97% ee). In addition, the absolute configuration of one product was determined. The Royal Society of Chemistry 2012.

Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4- ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids

A simple protocol for the Pd(OAc)2-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110°C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-onesand aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a largevariety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz,-OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenrichedα-aryl-substituted β-amino acids. We present a general approach for the synthesis of (2S)-isopropyl-5-aryl-2,3- dihydro-4(H)-pyrimidin-4-ones by Suzuki-Miyaura reaction of aryltrifluoroborate salts with(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones in the presence of a palladium catalyst and a base. The arylated compounds were transformed into enantioenriched α-aryl-substituted β-amino acids. Copyright

Organocatalysts and methods of use in chemical synthesis

The present invention is directed to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo