619306-98-8

Upstream product

• 1345336-02-8 C₂₁H₂₇NO₃ 
• 3081-24-1 H-Phe-OEt 
• 391642-61-8 N-(3-hydroxypropyl)-L-phenylalanine ethyl ester 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1384423-52-2 (S)-(1,2-dibenzylpyrrolidin-2-yl)methanol 
• 1384423-56-6 (R)-1,3-dibenzyl-3-fluoropiperidine 
• 1012058-86-4 N-(3-bromopropyl)-N-(tert-butoxycarbonyl)phenylalanine 
• 918437-82-8 2-[2-(toluene-4-sulfonyloxy)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 619306-99-9 (S)-N-(tert-butoxycarbonyl)-α-benzylproline ethyl ester 

Relevant academic research and scientific papers

Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: Synthesis of cyclic amines with a tertiary fluorine at C3

As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of

OPTICALLY ACTIVE CYCLIC AMINO ACID DERIVATIVE, ITS INTERMEDIATE AND THEIR MANUFACTURING METHODS

PROBLEM TO BE SOLVED: To provide a new cyclic amino acid derivative useful as a synthetic intermediate for drugs and agricultural chemicals, its intermediate, and a method of manufacturing the compound having high general-purpose properties which can be applied to 4- to 6-membered rings and can obtain a target product with an extremely high optical selectivity. SOLUTION: The optically active amino acid derivative represented by formula (1) is obtained by derivatizing an optically active amino acid represented by formula (3) as a raw material to an N-haloalkylamino acid derivative represented by formula (2) and reacting the compound with a base.

Asymmetric Cyclization via Memory of Chirality: A Concise Access to Cyclic Amino Acids with a Quaternary Stereocenter

N-(ω-Bromoalkyl)-amino acid derivatives, readily prepared from natural α-amino acids, gave cyclic amino acids with a quaternary stereocenter by treatment with potassium hexamethyldisilazaide in DMF. The chirality of parent amino acids was almost completely preserved during an enolate-formation and cyclization process, giving aza-cyclic amino acids in up to 98% ee in retention of configuration. This method is applicable to the asymmetric synthesis of azetidine, pyrrolidine, piperidine, and azepane derivatives. The asymmetric cyclization seems to proceed via an axially chiral enolate intermediate and not through a concerted SEi process. Copyright