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An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines

Coralie Kison, Nino Meyer, Till Opatz*

*Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany, Email:

C. Kison, N. Meyer, T. Opatz, Angew. Chem. Int. Ed., 2005, 44, 5662-5664.

DOI: 10.1002/anie.200501705


The selective aldimine cross-coupling represents a simple and flexible method for the synthesis of highly substituted unsymmetrical 1,2-diamines. In addition, either the syn- or anti-configurated vicinal diamine can be obtained, depending on the choice of the workup and reduction conditions.

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Key Words

CC coupling, carbanions, diamines, reduction, umpolung, borane, sodium borohydride, sodium cyanoborohydride

ID: J06-Y2005-1310