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Synthesis 1990; 1990(11): 1023-1024
DOI: 10.1055/s-1990-27082
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An Efficient and Practical Route to Enantiomerically Pure (+)-(1R,2R)- and (-)-(1S,2S)-1,2-Diphenylethane-1,2-diamines

D. Pini* , A. Iuliano, C. Rosini, P. Salvadori
  • *Centro di Studio del C.N.R. per le Macromolecole Stereordinate ed Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Universitá di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy
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Publikationsdatum:
17. September 2002 (online)

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The synthesis of the title compounds is easily achieved by the asymmetric Sharpless dihydroxylation of trans-stilbene to the corresponding enantiomerically pure diols. The conversion of the diols to the di-p-toluenesulfonates and subsequent reaction with sodium azide affords the diazides, which are reduced by lithium aluminum hydride to the optically pure 1,2-diamines.