173167-55-0

Upstream product

• 139224-87-6 N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-aminobenzeneacetonitrile 
• 175226-70-7 (5R)-3,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one 
• 2935-35-5 (S)-2-phenylglycine 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 73713-21-0 (4R)-2-benzyl-4-phenyl-2-oxazoline 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 
• 56613-80-0 D-2-phenylglycinol 
• 764625-36-7 (S)-Amino-phenyl-acetic acid 2-oxo-2-phenyl-ethyl ester 

Downstream Products

• 173242-81-4 (4R,6aS,9aR,9bS)-8-Methyl-4,9b-diphenyl-hexahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-c][1,4]oxazine-1,7,9-trione 
• 195528-62-2 (4R,8S,8aR)-8-Methyl-4,8a-diphenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one 
• 195528-52-0 (4R,8S,8aR)-8-Methyl-4,8a-diphenyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,6-dione 
• 173167-66-3 (4R,6aR,9aS,9bS)-4,8,9b-Triphenyl-hexahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-c][1,4]oxazine-1,7,9-trione 

Relevant academic research and scientific papers

Oxidative rearrangement of 2-substituted oxazolines. A novel entry to 5,6-dihydro-2H-1,4-oxazin-2-ones and morpholin-2-ones

A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important 'chiral glycine' synthons for asymmetric synthesis of α-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of α-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a 'nitrilium to acylium' 1,2-migration.

Synthesis of α-Phenyl Proline Derivatives via 1,3-Dipolar Cycloaddition of Chiral Stabilised Azomethine Ylids.

The preparation of (3S,5R)-3,5-diphenylmorpholinone 1 and subsequent diastereoselective 1,3-dipolar cycloaddition of its formaldehyde derived azomethine ylid is described.Removal of the chiral template furnishes α-phenyl proline derivatives.

α-Phenylglycinol as chiral auxiliary in diastereoselective Strecker synthesis of α-amino acids

The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative clearange make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular mechanics calculations are carried out to explain the observed diastereoselection.