Preparation of C3-symmetric homochiral syn-trisnorbornabenzenes through regioselective cyclotrimerization of enantiopure iodonorbornenes

A. F.G.Masud Reza, Shuhei Higashibayashi, Hidehiro Sakurai

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28 Citations (Scopus)

Abstract

C3-symmetric homochiral (-)-syn-trisoxonorbornabenzene 1 possessing a rigid cup-shaped structure was synthesized through a novel regioselective cyclotrimerization of enantiopure iodonorbornenes catalyzed by palladium nanoclusters. The yield of the cyclotrimerization was dependent on the stability of the palladium clusters, which was ascertained from the appear- ance and TEM images of the reaction mixtures. The efficient preparation of (-)-syn-1 was established in short steps, including the newly developed cyclotrimerization reaction. The thus- prepared homochiral (-)-syn-1 can serve as a key intermediate for the synthesis of C3-symmetric homochiral cup-shaped molecules with a helical arrangement of substituents. Introduction of several types of substituents was well demonstrated through palladium-catalyzed coupling reactions with the corresponding phosphate and triflate of (-)-syn-1.

Original languageEnglish
Pages (from-to)1329-1337
Number of pages9
JournalChemistry - An Asian Journal
Volume4
Issue number8
DOIs
Publication statusPublished - 2009 Aug 3

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Keywords

  • Cyclotrimerization helicity
  • Homochirality
  • Norbornene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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