4740-47-0

Usage

InChI:InChI=1/C10H13NO3/c11-10(7-12,9(13)14)6-8-4-2-1-3-5-8/h1-5,12H,6-7,11H2,(H,13,14)/t10-/m1/s1

Upstream product

• 1218797-22-8 4-benzyl-2-phenyl-2-oxazoline-4-carboxylic acid methyl ester 
• 1393737-33-1 diethyl 2-benzyl-2-(N-((R)-α-methylbenzyl)amino)malonate 
• 1393737-37-5 (R)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol 
• 1393737-43-3 (4S,αR)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone 
• 1393737-58-0 (S)-4-benzyl-4-hydroxymethyl-2-oxazolidinone 
• 1393737-25-1 diethyl 2-benzyl-2-(N-((R)-α-methylbenzyl)amino)malonate hydrochloride 
• 365402-94-4 (S)-(+)-2-amino-2-hydroxymethyl-3-phenylpropionic acid methyl ester 
• 1562415-38-6 (R)-1-benzhydryl 3-(tert-butyl)-2-bromo-2-benzylmalonate 
• 51127-28-7 (RS)-5-benzoylamino-5-benzyl-4-oxo-1,3-dioxane 
• 52421-48-4 (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid 
• 186904-44-9 (R)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 2-oxo-3-phenyl-propyl ester 
• 186904-46-1 (3R,5R)-3-Benzyl-5-isopropyl-6-oxo-morpholine-3-carbonitrile 
• 4982-08-5 1-hydroxy-3-phenylpropan-2-one 

Downstream Products

• 849622-98-6 3-[(2-amino-2-benzyl-3-hydroxypropoxy)methyl]-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzamide 

Relevant academic research and scientific papers

Enantioselective Synthesis of Chiral α-Azido and α-Aryloxy Quaternary Stereogenic Centers via the Phase-Transfer-Catalyzed α-Alkylation of α-Bromomalonates, Followed by SN2 Substitution

A new efficient synthetic method for chiral α-azido-α-alkylmalonates and α-aryloxy-α-alkylmalonates was developed. The enantioselective α-alkylation of diphenylmethyl tert-butyl α-bromomalonate under phase-transfer catalytic conditions [(S,S)-3,4,5-trifluorophenyl-NAS bromide, 50% KOH, toluene, and ?40 °C) provided the corresponding α-bromo-α-alkylmalonates in high chemical yields (≤98%) and high optical yields (≤99% ee). The resulting α-alkylated products were converted to α-azido-α-alkylmalonates (≤96%, ≤97% ee) and α-aryloxy-α-alkylmalonates (≤79%, ≤93% ee) by SN2 substitution with sodium azide and aryloxides, respectively.

Construction of chiral α-amino quaternary stereogenic centers via phase-transfer catalyzed enantioselective α-alkylation of α-amidomalonates

An efficient enantioselective synthetic method for α-amido-α-alkylmalonates via phase-transfer catalytic α-alkylation was successfully developed. The α-alkylation of α-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, 40 °C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding α-amido-α-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing α-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural α-amino acid.

Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377

A reaction of (S)-2-benzyl-2-(α-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(α-hydroxymethyl)phenylalanine (7) in two steps. N-Boc-α-methylphenylalanine (8), cericlami0ne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation.

Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate

Described is the development of a new solid-phase synthetic method for α-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported

Enantioselective synthetic method for α-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam

An enantioselective synthetic method for α-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic a-alkylation of 4a using P2-Et at -78 °C gave α-alkylation

Highly enantioselective synthesis of (R)-α-alkylserines via phase-transfer catalytic alkylation of o-biphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester using cinchona-derived catalysts

(Chemical Equation Presented) A highly enantioselective synthetic method for (R)-α-alkylserines was developed by the phase-transfer catalytic alkylation of obiphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester (4i) using cinchona-derived phase-transfer

Highly enantioselectlve phase-transfer-catalytic alkylation of 2-phenyl-2-oxazoline-4-carboxylic acid tert-butyl ester for the asymmetric synthesis of α-alkyl serines

A facile synthesis of chiral α-alkyl serines 3 involves the asymmetric alkylation of substrates 1 with alkyl halides (RX) under phase-transfer catalysis (PTC), followed by acidic hydrolysis of the alkylation products 2. The phenyl oxazoline moiety enhance

An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: Practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

Practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The α-alkylation and β-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives α-alkylation (up to >99%), and t-BuOK in DMF gives β-elimination (98%).

The origin of chemical and configurational stability of chiral nonracemic tert-butyl aziridinecarboxylate anions

The origin of good chemical and configurational stability of aziridine ester anions derived from (R)-(-)-phenylglycinol has been investigated. Kinetic acidity seems to play an important role in the deprotonation step and chemical stability of the anionic species. Spectroscopic investigations showed that the good overall retention of configuration was governed by the directing effect of the nitrogen atom, which acts as a stereogenic centre in the alkylation step of the enolate intermediate.

Aziridine mediated asymmetric synthesis of α-benzylserine and α-n-butylserine

Regioselective hydrogenolysis of enantiopure 2-benzyloxyaziridine 2-carboxylates represents a general method for the asymmetric synthesis of α-substituted serines. The aziridines are readily prepared via an aza-Darzens reaction of the enolate of methyl 3-