CONJUGATE ADDITION-REACTIONS OF ALPHA-AMINOALKYLCUPRATES PREPARED FROM ORGANOSTANNYL TERT-BUTYLCARBAMATES

Alpha-aminoalkylcyanocuprates, readily available from alpha-aminoalkyl stannanes via the organolithium reagents, undergo efficient conjugate addition to both simple and sterically hindered enones. Effective conj ugate addition with cuprates prepared via direct deprotonation of tert -butylcarbamates is substrate and carbamate dependent but can be enhan ced by use of sparteine instead of TMEDA in the deprotonation step. Th e method provides the first synthetically viable procedure for introdu ction of alpha-aminoalkyl groups via conjugate addition chemistry.