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

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

研究成果: Article査読

29 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1329-1337
ページ数9
ジャーナルChemistry - An Asian Journal
4
8
DOI
出版ステータスPublished - 2009 8 3
外部発表はい

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

フィンガープリント 「Preparation of C<sub>3</sub>-symmetric homochiral syn-trisnorbornabenzenes through regioselective cyclotrimerization of enantiopure iodonorbornenes」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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