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. © 2004 Elsevier Ltd. All rights reserved.