132273-88-2

Upstream product

• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 75-07-0 acetaldehyde 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 
• 100-52-7 benzaldehyde 
• 74213-58-4 N-[(1R)-2-hydroxy-1-phenylethyl]benzamide 
• 98-88-4 benzoyl chloride 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 142342-60-7 (R)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-butyric acid ethyl ester 
• 142342-68-5 (S)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-butyric acid ethyl ester 
• 5303-65-1 (S)-ethyl 3-aminobutyrate 
• 5303-65-1 ethyl 3-(R)-methyl-β-alanine 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.

Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds

A new efficient and scalable route to chiral non-racemic α-substituted propargylamines is described. The reaction pathway consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R- (-)-phenylglycinol.

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%).