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

Periasamy, Mariappan ; Seenivasaperumal, Muthu ; Dharma Rao, Vutukuri (2004) Synthesis of new chiral amino ether derivatives: synthetic application of meso aziridinium ions prepared from β-amino alcohols Tetrahedron: Asymmetry, 15 (24). pp. 3847-3852. ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2004.10.026

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 C2-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.

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