Chemoselective, substrate-directed fluorination of functionalized cyclopentane beta-amino acids

Kiss, Lorand and Nonn, Melinda and Sillanpaa, Reijo and Haukka, Matti and Fustero, Santos and Fülöp, Ferenc (2016) Chemoselective, substrate-directed fluorination of functionalized cyclopentane beta-amino acids. Chemistry an Asian Journal, 11. pp. 3376-3381. ISSN 1861-471X

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Abstract

This work describes asubstrate-directed fluorination of some highly functionalized cyclopentanederivatives. The cyclic products incorporatingCH 2ForCHF2 moieties in their structure have been synthesized from diexo-o rdiendonorbornene b-aminoacids following astereocontrolled strat egy.The synthetic study was based on an oxidative transformationofthe ring carbon–carbon double bond of the norbornene b-amino acids, followed by transformation of the resulted „all cis“and „trans“diformyl intermediates by fluorination with „chemodifferentiation“.

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