Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Shuhei Higashibayashi, Hidehiro Sakurai

研究成果: Article

94 引用 (Scopus)

抜粋

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.

元の言語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
発行部数27
DOI
出版物ステータスPublished - 2008 7 9
外部発表Yes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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