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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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Santos Fustero, Laia Albert, Natalia Mateu, Gema Chiva, Javier Miró, Javier González, José Luis Aceña. Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: synthesis of pipecolic acid and iminosugar derivatives. Chemistry (Weinheim an der Bergstrasse, Germany). 2012 Mar 19;18(12):3753-64

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PMID: 22334380

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