Use of metalated enecarbamates in the squarate cascade. Direct access to highly functionalized 2,4-cyclooctadienones by intramolecular interception of the mesocyclic dienolates

Leo A. Paquette, Jingsung Tae

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

A new method for constructing highly functionalized eight-membered ring ketones, fused to one or two additional rings as desired, is reported.

Original languageEnglish
Pages (from-to)3151-3154
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number18
DOIs
Publication statusPublished - 1997 May 5

Bibliographical note

Funding Information:
17 O 18 19 hetero atoms are bonded to the same cyclopentene. This interesting chemical transposition is made possible because the release of enolate anion 17 triggers transannular aldolization and generation of 18. In turn, the proximity factors that now develop allow for reintroduction of a cyclic carbamate moiety. Acknowledgment. The financial support of the National Science Foundation is gratefully acknowledged. X-ray crystallographic results were recorded by Prof. Robin Rogers and Dr. Judith Gallucci whom we thank.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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