Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Δ(9(12))-capnellene

Takashi Ohshima, Katsuji Kagechika, Midori Adachi, Mikiko Sodeoka, Masakatsu Shibasaki

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Abstract

An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.

Original languageEnglish
Pages (from-to)7108-7116
Number of pages9
JournalJournal of the American Chemical Society
Volume118
Issue number30
DOIs
Publication statusPublished - Jul 31 1996
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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