Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: Orthogonally protected di- and triaminocyclopentanecarboxylates

Melinda Nonn, Loránd Kiss, Eniko Forró, Reijo Sillanpää, Ferenc Fülöp

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A novel substrate-directed synthetic route to a series of highly functionalized, orthogonally protected di- or triaminocyclopentanecarboxylate derivatives with multiple chiral centres from an unsaturated bicyclic β-lactam has been accomplished by applying stereoselective ring C-C double bond aziridination with chloramine-T and phenyltrimethylammonium tribromide, followed by regioselective aziridine opening with different N,O nucleophiles and hydrides. The functionalization strategy was successfully extended for access to enantiomerically pure orthogonally protected triaminocarboxylates.

Original languageEnglish
Pages (from-to)8511-8519
Number of pages9
JournalTetrahedron
Volume70
Issue number45
DOIs
Publication statusPublished - Nov 11 2014

Keywords

  • Aziridine
  • Cispentacin
  • Enantiomers
  • Ring opening
  • Selective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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