Stereoselective allylation of chiral monoperoxyacetals

Aqeel Ahmed, Patrick H. Dussault

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.

Original languageEnglish (US)
Pages (from-to)4657-4670
Number of pages14
JournalTetrahedron
Volume61
Issue number19
DOIs
StatePublished - May 9 2005

Fingerprint

Allylation
Lewis Acids
Acetals
alkoxyl radical

Keywords

  • Allylation
  • Lewis acid
  • Monoperoxyacetal
  • Neighbouring group
  • Peroxide
  • Stereoinduction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective allylation of chiral monoperoxyacetals. / Ahmed, Aqeel; Dussault, Patrick H.

In: Tetrahedron, Vol. 61, No. 19, 09.05.2005, p. 4657-4670.

Research output: Contribution to journalArticle

Ahmed, Aqeel ; Dussault, Patrick H. / Stereoselective allylation of chiral monoperoxyacetals. In: Tetrahedron. 2005 ; Vol. 61, No. 19. pp. 4657-4670.
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