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Stereoselective Sc(OTf) 3 ‐Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals
Author(s) -
Wang PeterYong,
Massad Itai,
Marek Ilan
Publication year - 2021
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.202101634
Subject(s) - aldol reaction , stereoselectivity , enol , silylation , diastereomer , chemistry , aldehyde , catalysis , organic chemistry , aldol condensation , enol ether , silyl enol ether
Facile and modular access to stereodefined disubstituted aldehyde‐derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter‐intuitive stereochemical behavior of this Mukaiyama‐aldol reaction is accounted for by a non‐classical open transition state.