Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

Ian J.S. Fairlamb, Julia M. Dickinson, Ileana M. Cristea

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)3739-3742
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number19
DOIs
StatePublished - May 6 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Bicyclic aliphatic compounds
  • Cycloadditions
  • Ketenes
  • Palladium

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