Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Jane Totobenazara, Heloua Haroun, Julien Rémond, Karim Adil, Fabrice Dénès, Jacques Lebreton, Catherine Gaulon-Nourry*, Pascal Gosselin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

Original languageEnglish (US)
Pages (from-to)502-505
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number3
DOIs
StatePublished - Jan 21 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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