Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement: An Efficient Synthesis of (+)-Dihydromayurone

Eun Lee, In Jae Shin, Tae Seong Kim

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Abstract

(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond.

Original languageEnglish
Pages (from-to)260-264
Number of pages5
JournalJournal of the American Chemical Society
Volume112
Issue number1
DOIs
Publication statusPublished - 1990 Jan 1

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All Science Journal Classification (ASJC) codes

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

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