249734-39-2

Usage

Chemical compound

2-Azetidinecarboxylic acid, 1-[(1R)-1-phenylethyl]-, methyl ester, (2S)-

Structure

Complex

Derivative

Methyl ester of 2-azetidinecarboxylic acid

2-Azetidinecarboxylic acid

Cyclic amino acid

Chiral compound

Presence of 1-phenylethyl group

Stereochemistry

(2S)configuration at second carbon atom

Potential applications

Pharmaceutical or biochemical

Research needed

To fully understand properties and potential uses

Upstream product

• 29547-04-4 methyl 2,4-dibromobutanoate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 1206636-14-7 diphenyl-((2S)-1-((1R)-1-phenylethyl)azetidin-2-yl)-methanol 
• 924630-59-1 1-[1-(1-phenyl-ethyl)-azetidin-2-yl]-propan-1-one 
• 924630-57-9 1-(1-phenyl-ethyl)-azetidine-2-carboxylic acid methoxy-methyl-amide 
• 924630-61-5 2-chloro-4-[methoxycarbonyl-(1-phenyl-ethyl)-amino]-butyric acid methyl ester 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: Synthetic and mechanistic aspects

The scope and limitations of a novel intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams from azetidines in high regio- and stereoselectivity is reported. The key step of the process is a SN2-type ring-opening of TMSOTf-activated azetidine rings by silyl ketene acetals generated by treatment with TMSOTf and TEA. This study is a very rare example of nucleophilic ring-opening of azetidines that does not require formation of quaternary azetidinium salts by N-alkylation or the use of N-electron-withdrawing groups. Application of this process to 2-azetidinone system led to a complete change in reactivity and provide 6-aza-bicyclo[3.2.0]heptane derivatives via an unprecedented Mukaiyama aldol-like reaction involving an ester acceptor and a silyl imidate.

Enantioselective addition of alkynylzinc to arylaldehydes catalyzed by azetidino amino alcohols bearing an additional stereogenic center

Chiral azetidino amino alcohol ligands bearing an additional stereogenic center were readily prepared and used as catalysts for the asymmetric addition of alkynylzinc to aromatic aldehydes with enantioselectivities of up to 87% ee. The relationship betwee

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.