Stereoselective Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers by Iridium-Catalyzed Alkene
Itai Massad1, Heiko Sommer1, Ilan Marek1
1Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa, 3200009, Israel.
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.
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