Stereoselective Sc(OTf)3 -Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals

Angew Chem Int Ed Engl. 2021 Jun 1;60(23):12765-12769. doi: 10.1002/anie.202101634. Epub 2021 May 6.

Abstract

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.

Keywords: Mukaiyama-aldol reaction; acetals; enolates; scandium; selectivity.