Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Shuhei Higashibayashi; Hidehiro Sakurai

doi:10.1021/ja802822k

Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Shuhei Higashibayashi, Hidehiro Sakurai

研究成果: Article › 査読

96 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
巻	130
号	27
DOI	https://doi.org/10.1021/ja802822k
出版ステータス	Published - 2008 7 9
外部発表	はい

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

文献へのアクセス

10.1021/ja802822k

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引用スタイル

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