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synthesis of cis- and trans-3-aminocyclohexanols by reduction of β-enaminoketones合成顺式和trans-3-aminocyclohexanolsβ-enaminoketones的减少.pdf

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Molecules 2012, 17, 151-162; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of cis- and trans-3-Aminocyclohexanols by Reduction of β-Enaminoketones Iris Montoya Balbás, Blanca Eda Domínguez Mendoza, Mario Fernández-Zertuche, Mario Ordoñez and Irma Linzaga-Elizalde * Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Mor., CP 62209, Mexico * Author to whom correspondence should be addressed; E-Mail: linzaga@uaem.mx; Tel.: +52-77-7329-7997. Received: 25 October 2011; in revised form: 21 December 2011 / Accepted: 22 December 2011 / Published: 27 December 2011 Abstract: We describe a protocol developed for the preparation of β-enaminoketones derived from 1,3-cyclohexanediones, and their subsequent reduction by sodium in THF-isopropyl alcohol to afford cis- and trans-3-aminocyclohexanols. Keywords: 1,3-amino alcohols; 3-aminocyclohexanols; β-enaminoketones; reduction of β-enaminoketones 1. Introduction Amino alcohols are of great interest because of their biological and structural importance. For example, acyclic 1,3-amino alcohols are key structural components of numerous natural products [1-6], potent drugs [7,8], and components of numerous medicinal compounds such as HIV-protease inhibitors [9], μ-opioid receptor antagonists [10], potent antibiotic negamycin [11-13], serotonin reuptake inhibitor, and antidepressants
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