Modulating the stereochemical outcome of the Ireland-Claisen reaction of (E)- and (Z)-allylic glycolates

Ken S. Feldman, Brandon R. Selfridge

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R 2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.

Original languageEnglish (US)
Pages (from-to)825-828
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number7
DOIs
StatePublished - Feb 15 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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