STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-DIAMINO NITRILES FROM AMINO-ACIDS

alpha-Amino acids 1 are readily converted into the corresponding N,N-d ibenzylamino aldehydes 2 which in turn serve as starting materials for enantiomerically pure alpha-N,N-dibenzylamino aldimines 5, 6 and 7 ha ving benzyl, tosyl and trimethylsilyl groups, respectively, at the ald imine nitrogen atom. All three classes of chiral aldimines undergo ste reoselective Lewis acid promoted Me(3)SiCN addition reactions with non -chelation controlled formation of the corresponding alpha,beta-diamin o nitriles. All of the reaction sequences occur without any racemizati on.