1379761-96-2Relevant academic research and scientific papers
Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: Synthesis of pipecolic acid and iminosugar derivatives
Fustero, Santos,Albert, Laia,Mateu, Natalia,Chiva, Gema,Miro, Javier,Gonzalez, Javier,Acena, Jose Luis
, p. 3753 - 3764 (2012)
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
