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

13 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
Externally publishedYes

Bibliographical note

Funding Information:
I thank A. Kost, D. Williams, and J. Washizaki for excellent electron microscopy and photography. This work was supported by grants from the National Science Foundation and the National Institute of General Medical Sciences.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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