140170-63-4

Upstream product

• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 123-38-6 propionaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 74213-58-4 N-[(1R)-2-hydroxy-1-phenylethyl]benzamide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 142342-62-9 (R)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-pentanoic acid ethyl ester 
• 142342-70-9 (S)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of α-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines

A simple and general asymmetric synthesis of α-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-α-substituted amino phosphonic acids in good overall yields and high ee (77→97%) after simple deprotection.

Stereoselective ring opening of chiral oxazolidines by reformatsky reagents: An enantioselective entry to β-amino esters

Chiral oxazolidines obtained by condensation of aldehydes with (-).(R)- or (+).(S)-N-benzylphenylglycinol react with the Reformatsky reagent derived from ethyl bromoacetate, in mild reaction conditions (Et2O or CH2Cl2, 0°C, 15-60 min), leading to ethyl β-amino carboxylates in moderate to good diastereomeric excess (60-92%). These ring opening products are transformed into primary β-aminoesters, in one step, by debenzylation with H2/Pd on carbon without loss of their stereochemical integrity. In this way, ethyl β-amino carboxylates can be obtained in both enantiomeric forms, with chemical yields ranging 55-76% and moderate to good e.e. (60-92%).