194149-77-4

Upstream product

• 104665-17-0 ethyl 4-ethyl-5-oxopentanoate 
• 56613-80-0 D-2-phenylglycinol 
• 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 
• 66757-48-0 methyl 4-formylhexanoate 

Downstream Products

• 601489-05-8 tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate 
• 1273047-82-7 (3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-3,5,8,8atetrahydro-5H-oxazolo[3,2-a]pyridine 
• 1273047-73-6 (3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-6-(phenylselenyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 601489-07-0 tert-butyl (3R,5R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]piperidine-3-acetate 
• 890149-99-2 tert-butyl (3R,5R)-1-(tert-butoxycarbonyl)-5-ethylpiperidine-3-acetate 
• 439084-93-2 (5R,6R)-5-ethyl-6-phenyl-2-piperidone 
• 908572-67-8 (5R,6R)-6-allyl-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone 
• 908572-92-9 (5R,6R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-6-phenyl-2-piperidone 
• 908572-98-5 (5R,6S)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-6-vinyl-2-piperidone 
• 908572-82-7 (5R,6S)-5,6-diethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone 
• 908572-63-4 (5R,6R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-6-(3-indolyl)-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.

Dynamic kinetic resolution and desymmetrization processes: A straightforward methodology for the enantioselective synthesis of piperidines

A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols with racemic or prochiral δ-oxo (di)acid derivatives in highly stereoselective processes involving dynamic kinetic resolution and/or desymmetrization of diastereotopic or enantiotopic ester groups.

Alkylation of phenylglycinol-derived oxazolopiperidone lactams. Enantioselective synthesis of β-substituted piperidines

The stereochemical outcome of the alkylation of a variety of phenylglycinol-derived oxazolopiperidone lactams is studied. The influence of the configuration of the C-8a stereocenter and the effect of the substituents at the C-8 and C-8a positions on the s

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