185396-36-5

Upstream product

• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 52421-48-4 (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid 
• 51127-28-7 (RS)-5-benzoylamino-5-benzyl-4-oxo-1,3-dioxane 
• 1562415-38-6 (R)-1-benzhydryl 3-(tert-butyl)-2-bromo-2-benzylmalonate 
• 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 
• 365402-91-1 E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine 
• 365402-92-2 methyl E-(2S,3S)-(-)-2-benzyloxymethyl-3-phenyl-1H-aziridine-2-carboxylate 
• 365402-93-3 (S)-(+)-2-amino-2-benzyloxymethyl-3-phenylpropionic acid methyl ester 
• 262378-82-5 (S)-2-Benzyl-1-((R)-2-methoxy-1-phenyl-ethyl)-aziridine-2-carboxylic acid tert-butyl ester 
• 100-39-0 benzyl bromide 
• 865144-71-4 (S)-4-benzyl-2-phenyl-1,3-oxazoline-4-carboxylic acid 
• 721401-61-2 (S)-4-benzyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

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

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.

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

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-

Asymmetric Syntheses of Both Enantiomers of α-Benzylserine and α-Carboxymethylserine

Both enantiomers of α-benzyl and α-carboxymethyl serines (1, 2) were efficiently synthesized starting with the known phenyl acetol via an intramolecular asymmetric Strecker synthesis.

α-Hydroxymethylphenylglycine and α-hydroxymethylphenylalanine: Synthesis, resolution, and absolute configuration

Racemic α-hydroxymethylphenylglycine and α-hydroxymethylphenylalanine have been synthesized by selective hydroxymethylation of oxazolones derived from phenylglycine and phenylalanine, and resolved into enantiomers by fractional crystallization of their di