Stereoselective Access to Fluorinated and Non??fluorinated Quaternary Piperidines: Synthesis of Pipecolic Acid and Iminosugar Derivatives

…, N Mateu, G Chiva, J Miró, J González…

Index: Fustero, Santos; Albert, Laia; Mateu, Natalia; Chiva, Gema; Miro, Javier; Gonzalez, Javier; Acena, Jose Luis Chemistry - A European Journal, 2012 , vol. 18, # 12 p. 3753 - 3764

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Citation Number: 16

Abstract

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 ...