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Synlett 2000; 2000(5): 0641-0643
DOI: 10.1055/s-2000-6598
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Asymmetric Synthesis of γ-Amino Ketones and Nitriles via β-Aminoethylation of SAMP-Hydrazones with Tosylaziridine

Dieter Enders* , Carsten F. Janeck, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax + 49(241)8888-127; E-mail: enders@rwth-aachen.de
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Publication Date:
31 December 2000 (online)

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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.

asymmetric synthesis - hydrazones - ring opening - aziridines - aminoethylation