Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Shuhei Higashibayashi, Hidehiro Sakurai

研究成果: Article査読

106 被引用数 (Scopus)

抄録

The first asymmetric synthesis of a chiral buckybowl, a C3 symmetric (C)-8,13,18-trimethylsumanene (1), was achieved by employing a synthetic strategy that translates chirality at sp3 centers into bowl chirality. The synthesis features a syn selective cyclotrimerization of an enantiopure halonorbornene derivative, tandem ring-opening/closing olefin metathesis reactions, and DDQ oxidation at low temperature. The bowl-to-bowl inversion energy of 1 was determined as 21.6 kcal/mol by circular dichroism spectra measurement.

本文言語English
ページ(範囲)8592-8593
ページ数2
ジャーナルJournal of the American Chemical Society
130
27
DOI
出版ステータスPublished - 2008 7月 9
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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