Substrate-dependent fluorinations of highly functionalized cycloalkanes

L. Kiss, Attila Márió Remete, Melinda Nonn, Santos Fustero, Reijo Sillanpää, F. Fülöp

Research output: Article

7 Citations (Scopus)

Abstract

Substrate-dependent fluorinations of several highly functionalized cycloalkanes with multiple stereocentres were investigated. The synthetic transformations were based on selective functionalization of the ring C=C bonds of the readily available bicyclic β-lactams by epoxidation and regioselective nucleophilic oxirane opening with azide or cyanide, followed by hydroxy-fluorine exchange with Deoxofluor. Depending on the substituents and their relative steric arrangement, the attempted fluorinations produced different types of substituted cycloalkanes. These selective, substrate-directed synthetic procedures and their presumed pathways towards interesting highly functionalized fluorinated cycloalkane scaffolds were investigated.

Original languageEnglish
Pages (from-to)781-787
Number of pages7
JournalTetrahedron
Volume72
Issue number6
DOIs
Publication statusPublished - febr. 11 2016

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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