Abstract
The asymmetric synthesis of g-amino nitriles 4a-c and g- amino ketones 5d-f is described. Key step of the procedure is the diastereoselective b-aminoethylation of metalated SAMP-/RAMP- hydrazones 1a-f with tosylaziridine 2. Cleavage of the chiral auxiliary with MMPP leads to g-amino nitriles 4a-c in good yields and excellent enantiomeric excesses (ee ≥ 98%). Likewise g-amino ketones 5d-f (ee ≥ 98%) were obtained in good overall yields by cleavage of the hydrazones 3d-f with aqueous copper(II) chloride solution.
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