Asymmetric catalytic oxidative cleavage of polycyclic systems: the synthesis of atropisomeric diazonanes and diazecanes

Alan M. Jones, Gu Liu, Magali M. Lorion, Stephen Patterson, Tomas Lebl, Alexandra M. Z. Slawin, Nicholas J. Westwood

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Oxidative cleavage of internal double bonds in polycyclic systems can give access to compounds containing medium-to large-sized rings. In this example, the nine-and ten-membered ring containing compounds that resulted from the mCPBA-mediated (mCPBA = meta-chloroperoxybenzoic acid) oxidative cleavage reaction were shown to exhibit atropisomerism. The reaction of the polycyclic system with catalytic amounts of ruthenium tetra-oxide followed by diol cleavage achieved the same synthetic goal. Use of the Nishiyama-Beller ruthenium-based catalysts enabled the synthesis of optically-enriched samples, providing the first example of an atropselective oxidative cleavage reaction.

Original languageEnglish
Pages (from-to)5714-5718
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number20
DOIs
Publication statusPublished - May 2011

Keywords

  • asymmetric catalysis
  • atropisomerism
  • medium-sized ring synthesis
  • oxidative cleavage
  • ruthenium
  • synthetic methods
  • RUTHENIUM COMPLEXES
  • ALKENE EPOXIDATION
  • SUPERQUAT ENAMIDES
  • AXIAL CHIRALITY
  • CORE STRUCTURE
  • LIGANDS
  • OLEFINS
  • FUNCTIONALIZATION
  • DERIVATIVES
  • RING

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