Chiral silyl ketene acetals from thioesters

Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates

Patrick H Dussault, Tony K. Trullinger, Su Cho-Shultz

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The Lewis acid-mediated reaction of chiral O- and S-silyl ketene acetals (SKAs) with peroxyacetals and acetals was investigated as an approach to the asymmetric synthesis of 3-peroxy- and 3-alkoxyalkanoates. SKAs derived from chiral O-acetates fail to react with peroxyacetals and provide little diastereoselection in reactions of nonperoxidic acetals. Reaction of thioacetate SKAs with peroxyacetals furnishes 3-peroxyalkanoate thioesters in good yield but with poor diastereoselection. In the case of silyl ketene acetals based upon a camphorsulfonamide chiral auxiliary the diastereomeric peroxyalkanoates are easily separated. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)9213-9220
Number of pages8
JournalTetrahedron
Volume56
Issue number47
DOIs
StatePublished - Nov 17 2000

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Acetals
Lewis Acids
ketene
alkoxyl radical
Acetates

Keywords

  • Chiral auxiliary
  • Peroxide
  • Silyl ketene acetal
  • Thioester

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chiral silyl ketene acetals from thioesters : Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates. / Dussault, Patrick H; K. Trullinger, Tony; Cho-Shultz, Su.

In: Tetrahedron, Vol. 56, No. 47, 17.11.2000, p. 9213-9220.

Research output: Contribution to journalArticle

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