285988-23-0Relevant articles and documents
Asymmetric synthesis of γ-amino ketones and nitriles via β-aminoethylation of SAMP-hydrazones with tosylaziridine
Enders, Dieter,Janeck, Carsten F.,Runsink, Jan
, p. 641 - 643 (2007/10/03)
The asymmetric synthesis of γ-amino nitriles 4a-c and γ-amino ketones 5d-f is described. Key step of the procedure is the diastereoselective β-aminoethylation of metalated SAMP-/RAMP-hydrazones 1a-f with tosylaziridine 2. Cleavage of the chiral auxiliary with MMPP leads to γ-amino nitriles 4a-c in good yields and excellent enantiomeric excesses (ee ≥ 98%). Likewise γ-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. Thieme Stuttgart.