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Synlett 1997; 1997(2): 177-178
DOI: 10.1055/s-1997-729
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A Simple and Highly Diastereoselective One-Pot Synthesis of 1,3-Diamines

Beatrix Merla, Michael Arend, Nikolaus Risch*
  • *Fachbereich Chemie und Chemietechnik, Universität-Gesamthochschule Paderborn, Warburger Str. 100, D-33098 Paderborn, Germany, Fax +5251/60-3245; E-mail: nr@chemie.uni-paderborn.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A convenient one-pot procedure for the highly diastereoselective synthesis of 1,3-diamines 4 from inexpensive starting materials is described. Enamines 2 are aminoalkylated with preformed ternary iminium salts 1 yielding exclusively the quaternary iminium salts 3. In situ reduction of 3 with NaBH4/MeOH provides a broad access to the diastereomerically pure 1,3-diamines 4 in moderate to good yields.

1,3-diamines - diastereoselective aminoalkylation - diastereoselective reduction - enamines - iminium salts