Asymmetric Synthesis of a Chiral Buckybowl, Trimethylsumanene

2008/06/14 by Shuhei Higashibayashi, Hidehiro Sakurai · 2 citations
Chemistry · #Synthetic Organic Chemistry Methods #Synthesis and Properties of Aromatic Compounds #Asymmetric Synthesis and Catalysis

paper · doi:10.1021/ja802822k

openalex publication_date 2008/06/14 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/13

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.

Citations

• A Synthesis of Sumanene, a Fullerene Fragment
• Structural Elucidation of Sumanene and Generation of Its Benzylic Anions

Cited by

• A Chiral Concave‐Bound Cyclopentadienyl Iron Complex of Sumanene
• Sumanene [wikipedia]

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