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Synthesis 2011(6): 924-928  
DOI: 10.1055/s-0030-1258430
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Hydroxy- and Polyhydroxy-Substituted 1,3-Diaminocyclohexanes

Anobick Sar, Sergey Lindeman, William A. Donaldson*
Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881, USA
Fax: +1(414)2887066; e-Mail: william.donaldson@marquette.edu;
Further Information

Publication History

Received 22 October 2010
Publication Date:
10 February 2011 (online)

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Abstract

The synthesis of hydroxy-trans-1,3-diaminocyclo­hexanes based on nitroso-Diels-Alder cycloaddition of (cyclohexadienyl)phthalimide is reported.

Key words

cycloaddition - regioselectivity - amino alcohols - enantiomeric resolution

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The crystallographic data has been deposited with the CCDC for compounds (±)-7 (CCDC 778910), (±)-10 (CCDC 778911), and (±)-14 (CCDC 778912), respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.ccdc.cam.ac.uk. For the ORTEPs of (±)-7 and (±)-10 see Supporting Information.