245338-82-3

Basic information

• Product Name: N-4-fluorobenzylidene-DL-Ala isopropyl ester
• CAS NO: 245338-82-3
• Molecular Weight: 237.274
• Mol File: 245338-82-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-4-fluorobenzylidene-DL-Ala isopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-4-fluorobenzylidene-DL-Ala isopropyl ester(245338-82-3)
• EPA Substance Registry System: N-4-fluorobenzylidene-DL-Ala isopropyl ester(245338-82-3)

Safety Data

• Hazardous Substances Data: 245338-82-3(Hazardous Substances Data)

Upstream product

• 39825-33-7 isopropyl ester of alanine 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 30990-90-0 (S)-α-methyl-phenylalanine hydrochloride 
• 14603-77-1 (R)-α-methyl-phenylalanine hydrochloride 

Relevant articles and documents

Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids

It is shown that sodium alkoxides formed from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethanol) ((R,R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methytphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61-93% yields and with ee 69-94%. When (S,S)-TADDOL is used, the (3)-amino acid is formed. A mechanism explaining the observed features of the reaction is proposed.