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

L. Kiss, Melinda Nonn, Reijo Sillanpää, Matti Haukka, Santos Fustero, F. Fülöp

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

This work describes a substrate-directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH2F 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“.

Original languageEnglish
Pages (from-to)3376-3381
Number of pages6
JournalChemistry - An Asian Journal
Volume11
Issue number23
DOIs
Publication statusPublished - Dec 6 2016

Keywords

  • amino acids
  • cyclization
  • fluorine
  • molecular diversity
  • substituent effects

ASJC Scopus subject areas

  • Chemistry(all)

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