Enantioselective synthesis of substituted indanones from silyloxyallenes

Jonathan A. Brekan, Troy E. Reynolds, Karl A Scheidt

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

(Chemical Equation Presented) A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6- pentamethylpiperidine and PdCl2(PPh3)2 (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

Original languageEnglish (US)
Pages (from-to)1472-1473
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number5
DOIs
StatePublished - Feb 10 2010

ASJC Scopus subject areas

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

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