Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: synthesis of pipecolic acid and iminosugar derivatives |
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Authors: | Fustero Santos Albert Laia Mateu Natalia Chiva Gema Miró Javier González Javier Aceña José Luis |
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Affiliation: | Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Valencia, Spain. santos.fustero@uv.es |
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Abstract: | 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 (TMSCF(3)) followed by iodoamination and migration of the CF(3) 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. |
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