Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids

Abstract

This work describes a substrate-directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH₂ F or CHF₂ moieties in their structure have been synthesized from diexo- or diendo-norbornene β-amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon-carbon double bond of the norbornene β-amino acids, followed by transformation of the resulted "all cis" and "trans" diformyl intermediates by fluorination with "chemodifferentiation".

Keywords: amino acids; cyclization; fluorine; molecular diversity; substituent effects.