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Issue 28, 2014
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Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives

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Abstract

Structurally diverse carbocycles with two vicinal nitrogen-substituents were prepared in expedient three-component reactions from simple amines, aldehydes, and nitroalkenes. trans,trans-6-Nitrocyclohex-2-enyl amines were obtained in a one-pot domino reaction involving condensation, tautomerisation, conjugate addition, and nitro-Mannich cyclisation. Upon employment of less nucleophilic carboxamides, a concerted Diels–Alder cycloaddition mechanism operated to give the corresponding cis,trans-nitrocyclohexenyl amides. Both types of substituted carbocycles offer ample opportunities for chemical manipulations at the core and periphery. Ring oxidation with MnO2 affords substituted nitroarenes. Reduction with Zn/HCl provides access to various trans- and cis-diaminocyclohexenes, respectively, in a straight-forward manner. With enantiopure secondary amines, a two-step synthesis of chiral nitrocyclohexadienes was developed (82–94% ee).

Graphical abstract: Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives

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Publication details

The article was received on 04 May 2014, accepted on 06 Jun 2014 and first published on 09 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB00913D
Citation: Org. Biomol. Chem., 2014,12, 5267-5277
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    Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives

    A. K. Weber, J. Schachtner, R. Fichtler, T. M. Leermann, J. M. Neudörfl and A. Jacobi von Wangelin, Org. Biomol. Chem., 2014, 12, 5267
    DOI: 10.1039/C4OB00913D

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