N-Trimethylsilyloxyenamines as new aldehyde enolate synthons: general, efficient and diastereoselective aldol reaction with ketals and acetals

Abstract

E-N-Trimethylsilyloxyenamines, easily accessible from aldonitrones, proved to be excellent nucleophiles in TMSOTfinduced diastereoselective aldol reaction, both with ketals and acetals, proceeding via an extended transition state and leading to a new aldol C–C-bond in the aldonitrone products, that can be readily hydrolysed to the corresponding aldehydes.

Keywords

• N-trimethylsilyloxyenamines
• aldol reaction
• diastereoselectivity
• trimethylsilyl trifluoromethanesulfonate