Stereoselective Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers by Iridium-Catalyzed Alkene Isomerization

Itai Massad, Heiko Sommer, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

An in situ generated cationic Ir-catalyst isomerizes simple allylic silyl ethers into valuable, fully substituted aldehyde-derived silyl enol ethers. Importantly, by judicious choice of substrate, either of the two possible stereoisomers of a given enolate derivative is accessible with complete stereoselectivity. One-pot isomerization-aldol and isomerization-allylation processes illustrate the synthetic utility of this method.

Original languageEnglish
Pages (from-to)15549-15553
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number36
DOIs
StatePublished - 1 Sep 2020

Keywords

  • alkene isomerization
  • enolates
  • iridium
  • quaternary centers

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Catalysis

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