244183-19-5

Upstream product

• 244183-18-4 (2S)-1-methyl-benzyl-2,3-dihydro-4-pyridone 
• 244183-01-5 (S)-2-benzyl-2,3-dihydropyridin-4(1H)-one 
• 244182-99-8 (2S)-1-[(((1S,2R)-trans-2-(α-cumyl)cyclohexyl)oxy)carbonyl]-2-benzyl-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 161693-64-7 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl chloroformate 
• 87604-57-7 (R)-2-(benzyloxy)-2-phenylacetaldehyde 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

Asymmetric synthesis of (1R,5S)-2-methyl-6,7-benzomorphan via Aza-Prins reaction

(1R,5S)-2-Methyl-6,7-benzomorphan has been synthesised from (R)-(benzyloxy)(phenyl)acetaldehyde. On a 2-mmol scale Bi (OTf)3 promoted Aza-Prins reaction with N-tosylhomoallylamine afforded an 88/12 mixture of 6-oxa-2-azabicyclo[3.2.1]octanes. Major diastereoisomer was converted to enantiomerically pure (2S,4S)-2-benzyl-1- methylpiperidin-4-ol via a high-yielding sequence hydrogenolysis/N-detosylation/N-methylation. Acid-catalysed intramolecular Friedel?Crafts cyclisation of the piperidinol afforded (1R,5S)-2-methyl-6,7-benzomorphan in five steps with a yield of 25%.

Enantiopure n-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of benzomorphans

(Matrix presented) Concise asymmetric syntheses of several benzomorphan derivatives have been accomplished using enantiopure 2,3-dihydro-4-pyridones as chiral building blocks.