194149-80-9

Upstream product

• 104665-17-0 ethyl 4-ethyl-5-oxopentanoate 
• 56613-80-0 D-2-phenylglycinol 
• 66757-48-0 methyl 4-formylhexanoate 
• 194149-76-3 (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Downstream Products

• 908573-16-0 (5S,6R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-6-phenyl-2-piperidone 
• 1273048-09-1 (3R,7R,8S,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 1273047-32-7 (3R,6S,7S,8S,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 1273047-85-0 (3R,8S,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-3,5,8,8atetrahydro-5H-oxazolo[3,2-a]pyridine 
• 439084-93-2 (5S,6R)-5-ethyl-6-phenyl-2-piperidone 

Relevant academic research and scientific papers

Stereoselective α-amidoalkylation of phenylglycinol-derived lactams. Synthesis of enantiopure 5,6-disubstituted 2-piperidones

The stereochemical outcome of α-amidoalkylation reactions of chiral nonracemic bicyclic lactams 2b and 2c with indole, allyltrimethylsilane, TMSCN and Grignard reagents to gain access to enantiopure 5,6-disubstituted 2-piperidones is discussed.

A concise procedure for the preparation of enantiopure 3-alkylpiperidines

Reaction of (R)-phenylglycinol with racemic methyl 4-formylhexanoate takes place with a remarkable stereoselectivity to give two diastereomeric 6-ethyloxazolopiperidones (9:1 ratio) in 76% overall yield. After LiAlH4 reduction and catalytic hyd