Reaction of peroxyacetals with silyl ketene acetals: Synthesis of 3- peroxyalkanoates and 3-peroxyalkanals

P. H. Dussault, R. J. Lee, J. A. Schultz, Y. S. Suh

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

Lewis acid-mediated reaction of monoperoxyacetals with silyl ketene acetals (SKAs) provides an efficient approach to 3-peroxyalkanoates. Propionate SKAs react with aliphatic peroxyacetals to furnish 3-peroxy-2- methyl alkanoates with modest anti-selectivity. Although acetate and thioacetate SKAs are less reactive, the latter react with unsaturated peroxyacetals to furnish peroxyalkenoates and -alkadienoates which undergo chemoselective reduction to 3-peroxyalkenals and 3-peroxyalkadienals. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)5457-5460
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number29
DOIs
StatePublished - Jul 15 2000

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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