18468-90-1Relevant articles and documents
Chemoenzymatic preparation of optically active trans-cyclohexane-1,2- diamine derivatives: An efficient synthesis of the analgesic U-(-)-50,488
Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
, p. 5788 - 5794 (2007/10/03)
Stereoespecific syntheses of (±)-trans-N,N-cyclohexane-1,2-diamines ((±)-4a-g) were carried out from the corresponding (±)-trans-N,N- dialkylaminocyclohexanols by successive treatment with mesyl chloride and aqueous ammonia. The stereochemical outcome indicates the formation of a meso-aziridinium ion intermediate, Kinetic resolutions of diamines (±)-4 were efficiently accomplished in aminolysis reactions catalyzed by lipase B from Candida antarctica with ethyl acetate as the solvent and acyl donor. Acetamides and the remaining diamines, isolated as the benzyloxycarbonyl derivatives, were obtained with very high ee values (92-99%), One of the carbamates was used as a precursor of the analgesic U-(-)-50,488.
