439084-69-2

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 1501-05-9 5-oxo-5-phenylvaleric acid 

Downstream Products

• 1049705-01-2 (3R,8aR)-6-(benzyloxycarbonyl)-5-oxo-3,8a-diphenyl-6-(phenylselenyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 890150-01-3 (2S,5S)-5-benzyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-phenylpiperidine 
• 3466-80-6 (R)-(+)-6-phenylpiperidine 
• 205526-48-3 (2S)-1-[(1R)-2-hydroxy-1-phenylethyl]-2-phenylpiperidine 
• 205526-55-2 (2R)-1-[(1R)-2-hydroxy-1-phenylethyl]-2-phenylpiperidine 
• 890149-82-3 (3R,6S,8aR)-6-benzyl-5-oxo-3,8a-diphenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Relevant academic research and scientific papers

Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine

Cyclodehydration of achiral or racemic aryl-δ-oxoacids with (R)-phenylglycinol stereoselectively affords chiral non-racemic bicyclic lactams, from which the enantiodivergent synthesis of (R)- and (S)-2-phenylpiperidine, the diastereodivergent synthesis of cis- and trans-3-ethyl-2-phenylpiperidine, and the enantioselective synthesis of the piperidine alkaloid (-)-anabasine is reported.

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.