Asymmetric synthesis of gamma-amino ketones and nitriles via beta-aminoethylation of SAMP-hydrazones with tosylaziridine

The asymmetric synthesis of gamma-amino nitriles 4a-c and gamma-amino keton es 5d-f is described. Key step of the procedure is the diastereoselective b eta-aminoethylation of metalated SAMP-/RAMP-hydrazones 1a-f with tosylaziri dine 2. Cleavage of the chiral auxiliary with MMPP leads to gamma-amino nit riles 4a-c in good yields and excellent enantiomeric excesses (ee greater t han or equal to 98%). Likewise gamma-amino ketones 5d-f (ee greater than or equal to 98%) were obtained in good overall yields by cleavage of the hydr azones 3d-f with aqueous copper(II) chloride solution.