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Synthesis 1996; 1996(1): 53-58
DOI: 10.1055/s-1996-4166
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Enantioselective Synthesis of Differently Protected 1,2-Diamines via α-Alkylation of Dibenzylaminoacetaldehyde SAMP-Hydrazone

Dieter Enders* , Robert Schiffers
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax +49(241)8888127; E-mail Enders@RWTH-Aachen.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Chiral, unsymmetrically and differently protected 1,2-diamines 4 were prepared in moderate to good overall yields and with high asymmetric inductions (ee = 91-99%) by α-alkylation of N,N-dibenzylaminoacetaldehyde SAMP-hydrazone (S)-2 with subsequent oxidative cleavage to the corresponding α-aminonitriles, reduction to the diamines, and protection of the latter.

asymmetric synthesis - 1,2-diamines - SAMP-hydrazones - α-alkylation - hydrazone/nitrile conversion