Synthesis of new chiral amino ether derivatives: synthetic application of meso aziridinium ions prepared from β-amino alcohols

Abstract

Methods of synthesis of new chiral amino ether derivatives through the opening of aziridinium ions, prepared in situ using trans-(±)-2-(1- N, N-dialkylamino)cyclohexyl mesylate with ( R)-(+)-1,1′-bi-2-naphthol, are described. The ( R, R, R)-diastereomer was obtained as the major product and isolated as an enantiopure salt, and characterized by single crystal X-ray analysis. The C 2-chiral ( R, R, R, R, R)-diamino ether was obtained as the major product by opening of the aziridinium ion, prepared using trans-(±)-2-(1-pyrrolidino)cyclohexyl mesylate and ( R)-(+)-1,1′-bi-2-naphthol in the presence of aq NaOH. This was also characterized by single crystal X-ray analysis.