Asymmetric synthesis of a chiral buckybowl, trimethylsumanene.

  title={Asymmetric synthesis of a chiral buckybowl, trimethylsumanene.},
  author={Shuhei Higashibayashi and Hidehiro Sakurai},
  journal={Journal of the American Chemical Society},
  volume={130 27},
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… CONTINUE READING

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For racemic synthesis of C3 symmetric chiral buckybowls, see ref 2d and e. For racemic synthesis of corannulene derivatives, see refs 1, 3b, and following references Tsefrikas

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Synthesis 1981, 1001–1003

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