213828-95-6

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 152615-80-0 (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 
• 177981-20-3 (6R)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-2-piperidone 
• 503843-26-3 (6R)-1-[(1R)-2-(tert-butyldimethylsilyloxy)-1-phenylethyl]-6-methyl-2-piperidone 

Downstream Products

• 28720-60-7 (2R,6R)-(-)-2-methyl-6-undecylpiperidine 
• 503843-27-4 (2R,6R)-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-undecylpiperidine 
• 217499-52-0 (2R,6S,1'R)-N-(2-hydroxy-1-phenylethyl)-2-methyl-6-undecylpiperidine 

Relevant academic research and scientific papers

Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam

Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.

Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A

The enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A from 6-methyl-2- piperidone 1 is described. The key step of this synthesis consists of the addition of a dialkylcopper derivative to the thioimidate salt 3 followed by sodium borohydride reduction of the resulting iminium salt.