Oxidative kinetic resolution-Claisen rearrangement sequence to enantioenriched arylcycloalkenes

David C. Ebner, Z. Novák, Brian M. Stoltz

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The Pd-catalyzed oxidative kinetic resolution of secondary alcohols afforded enantioenriched allylic alcohols with high selectivity. These alcohols were transformed into arylcycloalkenes with enantioenriched tertiary and quaternary stereocenters through a two-step vinylation and Lewis acid promoted Claisen rearrangement. Subsequent Pd-catalyzed oxidative cyclization of a Claisen product afforded a 5,5-fused tetrahydrofuran.

Original languageEnglish
Pages (from-to)3533-3539
Number of pages7
JournalSynlett
Issue number20
DOIs
Publication statusPublished - Dec 18 2006

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Alcohols
Lewis Acids
Kinetics
Cyclization
tetrahydrofuran
allyl alcohol

Keywords

  • Claisen rearrangement
  • Oxidative cyclization
  • Oxidative kinetic resolution
  • Palladium catalysis
  • Secondary alcohols

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Oxidative kinetic resolution-Claisen rearrangement sequence to enantioenriched arylcycloalkenes. / Ebner, David C.; Novák, Z.; Stoltz, Brian M.

In: Synlett, No. 20, 18.12.2006, p. 3533-3539.

Research output: Contribution to journalArticle

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