Stereoselective Synthesis of α-Silylamines by the Direct Addition of Silyl Anions to Activated Imines

Abstract

[reaction: see text] A highly efficient stereoselective synthesis of unusual alpha-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediates. The use of enantiopure tert-butanesulfinyl imines as the electrophiles affords exceedingly high levels of diastereocontrol for the newly formed stereogenic carbon.