Delineating the possibilities for intramolecular interception of the squarate ester cascade through the use of metalated enecarbamates

J. Tae, L. A. Paquette

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Highly functionalized and annulated 2,4-cyclooctadienones are formed in a stereoselective manner by sequential treatment of squarate esters with a lithiated enecarbamate (six-membered ring or larger) and a cycloalkenyl-or 1-alkenyllithium reagent. The mechanistic details of this multistep process are presented. Particular attention is drawn to the step that involves intramolecular nucleophilic attack by a proximal oxido anion at the carbamate carbonyl and results in redirection of the cascade. This step is thwarted when five-membered cyclic enecarbamates are employed because of the excessive buildup of ring strain in the associated transition state.

Original languageEnglish
Pages (from-to)689-696
Number of pages8
JournalCanadian Journal of Chemistry
Volume78
Issue number6
DOIs
Publication statusPublished - 2000 Jan 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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