Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Shuhei Higashibayashi, Hidehiro Sakurai

Research output: Contribution to journalArticle

90 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 languageEnglish
Pages (from-to)8592-8593
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number27
DOIs
Publication statusPublished - 2008 Jul 9
Externally publishedYes

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Chirality
Alkenes
Circular Dichroism
Temperature
Dichroism
Olefins
Derivatives
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Asymmetric synthesis of a chiral buckybowl, trimethylsumanene. / Higashibayashi, Shuhei; Sakurai, Hidehiro.

In: Journal of the American Chemical Society, Vol. 130, No. 27, 09.07.2008, p. 8592-8593.

Research output: Contribution to journalArticle

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