1379671-76-7

Upstream product

• 1379671-58-5 (-)-(4R,6S,9aS)-6-(iodomethyl)-4-phenyl-9a-(trifluoromethyl)-3,4,6,7-tetrahydropyrido[2,1-c][1,4]oxazin-1(9aH)-one 
• 1379671-69-8 (-)-(4R,6S,9aS)-6-(acetoxymethyl)-4-phenyl-9a-(trifluoromethyl)-3,4,6,7-tetrahydropyrido[2,1-c][1,4]oxazin-1(9aH)-one 
• 1009606-69-2 C₁₆H₁₆F₃I₂NO₂ 
• 1009605-87-1 (2R,5R)-3-(pent-4-enyl)-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-2-ol 
• 1009605-77-9 (R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 

Downstream Products

• 1379671-77-8 (-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-(diacetoxy)-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one 

Relevant academic research and scientific papers

Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: Synthesis of pipecolic acid and iminosugar derivatives

The preparation of optically pure quaternary piperidines, both fluorinated and non-fluorinated, has been achieved from a chiral imino lactone derived from (R)-phenylglycinol. In the case of the fluorinated derivatives, the addition of (trifluoromethyl)trimethylsilane (TMSCF3) followed by iodoamination and migration of the CF3 group allowed access to four derivatives of α-(trifluoromethyl)pipecolic acid. A theoretical study of the CF 3-group rearrangement has been carried out to help establish the reaction mechanism of this uncommon transformation. Moreover, a route to trifluoromethyl-substituted iminosugars was also developed through the diastereoselective dihydroxylation of suitable synthetic intermediates. Conversely, alkylation of the starting substrate and subsequent cross-metathesis and aza-Michael reactions led to α-alkyl derivatives of the target compounds. Copyright