247122-85-6

Upstream product

• 247122-82-3 tert-butyl (R,R,R)-(+)-4'-fluoro-2'-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylideneamino)pent-4'-enoate 

Downstream Products

• 1408282-75-6 tert-butyl (R)-N-(4-methoxyphenylsulfonyl)-γ-fluoro-α-aminopent-4-enoate 
• 1408283-09-9 (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamic acid 
• 1408283-01-1 O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate 
• 1408282-93-8 (R)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enoic acid 
• 1408282-85-8 tert-butyl (R)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enoate 

Relevant academic research and scientific papers

Enantioselective syntheses of 2-amino-4-fluoropent-4-enoic acids. Isosteres of asparagine

Diastereoselective alkylation of (R)-(+)-camphor-based glycine or alanine esterimines with 3-bromo-2-fluoropropene after hydrolytic deprotection gave (R)-(+)-2-amino-4-fluoropent-4-enoic acid with 38% overall yield and 90% ee, or (R)-(+)-2-amino-4-fluoro-2-methylpent-4-enoic acid (19% overall yield, 59% ee), respectively. Deprotection under drastic conditions was accompanied by hydrolysis of the fluorovinyl moiety to give (R)-(-)-2- amino-4-oxopentanoic acid hydrochloride with 28% overall yield and >95% ee. Ab initio calculations of acetamide and 2-fluoropropene as models for a primary amide or a fluorovinyl group despite of their different electronic structure show a similar electrostatic potential on the van der Waals surface suggesting their isosteric behavior.