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

Jinsung 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

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Carbamates
Anions
Esters
Negative ions

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

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Delineating the possibilities for intramolecular interception of the squarate ester cascade through the use of metalated enecarbamates. / Tae, Jinsung; Paquette, L. A.

In: Canadian Journal of Chemistry, Vol. 78, No. 6, 01.01.2000, p. 689-696.

Research output: Contribution to journalArticle

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