141548-84-7

Upstream product

• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 123-72-8 butyraldehyde 
• 98-88-4 benzoyl chloride 
• 74213-58-4 N-[(1R)-2-hydroxy-1-phenylethyl]benzamide 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 141548-81-4 (R)-2-[Benzyl-(1-propyl-hex-5-enyl)-amino]-2-phenyl-ethanol 
• 141548-80-3 (R)-2-[Benzyl-((R)-4-[1,3]dioxolan-2-yl-1-propyl-butyl)-amino]-2-phenyl-ethanol 
• 141565-31-3 (R)-2-[Benzyl-((S)-4-[1,3]dioxolan-2-yl-1-propyl-butyl)-amino]-2-phenyl-ethanol 
• 141548-83-6 (S)-6-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-nonan-2-one 
• 141548-82-5 (R)-6-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-nonan-2-one 
• 142342-63-0 (R)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester 
• 142342-71-0 (S)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-hexanoic 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%).

ASYMMETRIC SYNTHESIS OF PIPERIDINE ALKALOIDS UTILIZING DIASTEREOSELECTIVE REACTION OF 1,3-OXAZOLIDINE WITH GRIGNARD REAGENTS

A facile method of synthesizing enantiomerically pure piperidine alkaloids, (R)-(-)-coniine and (2R,6S)-(-)-dihydropinidine, has been explored by employing the highly diastereoselective reaction of a 1,3-oxazolidine with Grignard reagents.