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A new method for the preparation of unsymmetrical 1,4-substituted piperazine derivatives
Affiliation:1. Departamento de Quı́mica, Centro de Investigación y de Estudios Avanzados del IPN, Apdo. Postal 14-740, 07000 Mexico D.F., Mexico;2. Universidad Autónoma del Estado de Morelos, Centro de Investigaciones Quı́micas, Av. Universidad 1001, Col. Chamilpa C. P. 62210, Cuernavaca, Morelos, Mexico;3. Lab. de RMN, Universidad Autónoma Metropolitana, Av. Michoacan y la Purisima s/n, Col. Vicentina, 09340 Ixtapalapa, Mexico D.F., Mexico;1. State Key Laboratory of Freshwater Ecology and Biotechnology, Institute of Hydrobiology, Chinese Academy of Sciences, Wuhan 430072, China;2. University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:Symmetrical and unsymmetrical N,N′-piperazine derivatives of (−)-norephedrine and o-aminophenol were synthesized stereoselectively in yields >70% by reduction of the corresponding N,N′-ethylenebisoxazolidine heterocycles. The stereochemistry at the ring fusion carbons was established by NMR spectroscopy and X-ray crystallography.
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