N-TERT-BUTYLDIMETHYLSILYL IMINES AS INTERMEDIATES FOR THE SYNTHESIS OF AMINES AND KETONES

Grignard reagents add to benzonitrile at low temperature catalyzed by CuBr and TBSCl affording N-TBS ketimines, which were? investigated as intermediaries for the synthesis of primary amines and ketones. N-sily limines were easily obtained by an organolithium addition to benzonitr ile followed by a reaction with TBSCl in CH,CI,. In situ reduction of these imines by BH3 and 1,3,2-oxazaborolidines 1 or. 2 as chiral templ ates afforded the corresponding amines with modest to good enantiomeri c excess.