Asymmetric β-Aminoethylation of Ketones and Nitriles with Tosylaziridines Employing the SAMP-Hydrazone Method

Abstract

The nucleophilic ring-opening of tosylaziridines with chiral aza-enolates is reported. The SAMP-/ RAMP-hydrazones 1a−h derived from aldehydes or ketones were reacted with tosylaziridine 2a to give the β-aminoethylated hydrazones 3a−h with good diastereoselectivity. Removal of the chiral auxiliary resulted in the formation of the γ-amino nitriles 4a−e or γ-amino ketones 6f−h in good yields and excellent enantiomeric excesses (ee Ն 98%). Ring-opening of the enantiopure, benzyl-substituted tosylaziridine 2b with aza-en-