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Stereoselective Access to Fully Substituted Aldehyde‐Derived Silyl Enol Ethers by Iridium‐Catalyzed Alkene Isomerization
Author(s) -
Massad Itai,
Sommer Heiko,
Marek Ilan
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005058
Subject(s) - isomerization , iridium , silylation , enol , alkene , stereoselectivity , umpolung , aldehyde , catalysis , chemistry , photochemistry , organic chemistry , nucleophile
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.