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

Research output: Contribution to journal › Article › peer-review

112 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	8592-8593
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	27
DOIs	https://doi.org/10.1021/ja802822k
Publication status	Published - 2008 Jul 9
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja802822k

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abstract = "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.",

author = "Shuhei Higashibayashi and Hidehiro Sakurai",

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AB - 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.

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Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Abstract

ASJC Scopus subject areas

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