Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines.
[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.
Ballweg
David M
DM
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
Miller
Rebecca C
RC
Gray
Danielle L
DL
Scheidt
Karl A
KA