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

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.

Automated summary

The facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed for their successful application in a stereoselective aldol reaction, resulting in excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is explained by a non-classical open transition state.