177981-20-3

Upstream product

• 917-54-4 methyllithium 
• 152615-80-0 (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 
• 191470-38-9 (3R,8aS)-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 3128-06-1 5-ketohexanoic acid 
• 56613-80-0 D-2-phenylglycinol 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 204845-25-0 (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 191470-39-0 (-)-(3R,5R,8aS)-(5,8a)-dimethyl-3-phenyl-hexahydrooxazolo[3,2-a]pyridine 
• 175274-14-3 (2R)-1-[(1R)-2-hydroxy-1-phenylethyl]-2-methylpiperidine 
• 191470-40-3 (-)-(2'R)-((2R,6R)-2,6-dimethylpiperidin-1-yl)-2'-phenylethanol 
• 217499-52-0 (2R,6S,1'R)-N-(2-hydroxy-1-phenylethyl)-2-methyl-6-undecylpiperidine 
• 503843-27-4 (2R,6R)-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-undecylpiperidine 
• 28720-60-7 (2R,6R)-(-)-2-methyl-6-undecylpiperidine 
• 503843-17-2 (2R,6R)-2-[3-(1,3-dioxolan-2-yl)propyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine 
• 213828-95-6 (6R)-1-[(1R)-2-(tert-butyldimethylsilyloxy)-1-phenylethyl]-6-methyl-2-piperidinethione 
• 88057-00-5 (2R,6S)-1-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-propylpiperidine 
• 792183-69-8 (5R,9R)-5-methylindolizidine 
• 786638-03-7 (4R,9aS)-4-methylquinolizidine 
• 503843-20-7 (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine 
• 503843-26-3 (6R)-1-[(1R)-2-(tert-butyldimethylsilyloxy)-1-phenylethyl]-6-methyl-2-piperidone 

Relevant academic research and scientific papers

Stereoselective α-amidoalkylation reactions of phenylglycinol-derived bicyclic lactams

The stereochemical outcome of α-amidoalkylation reactions from the chiral non-racemic bicyclic lactams trans-1 and cis-1 using indole, allyltrimethylsilane, higher order organocuprates, TMSCN, and Grignard reagents is discussed.

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.

Asymmetric synthesis of (+) and (-) trans-2,6-dimethylpiperidines

(+) aid (-) trans-2,6-dimethylpiperidines 9 have been prepared from diastereomeric lactams 6 and 11, both available from (R)-(-)-phenylglycinol 4. Diastereoselective C-2 alkylation afforded oxazolidines 7 and 12. Reduction of 7 with LiAlH4 or NaBH4 led to trans-2,6-8 with total retention of configuration. When 12 was reduced with NaBH4, trans derivative 13a was isolated as the major isomer. A mechanism is proposed to explain the different results.

Synthesis of enantiopure piperidines. Total synthesis of (2R,6S)-2-methyl-6-propylpiperidine [(-)-dihydropinidine]

Enantiomerically pure 2-alkyl-, 3-alkyl-, 4-alkyl-, and cis-2,6-dialkylpiperidines are prepared from the chiral, non-racemic oxazolopiperidone 1. An asymmetric synthesis of (2R,6S)-(-)-dihydropinidine is reported.