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

Abstract

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

cycloaddition - regioselectivity - amino alcohols - enantiomeric resolution

References

<A NAME="RM07110SS-1A">1a</A> Wang J. Chang C.-WT. Aminoglucoside Antibiotics: From Chemical Biology to Drug Discovery   Ayra DP. John Wiley & Sons; Hoboken: 2007.  p.141 

<A NAME="RM07110SS-1B">1b</A> Busscher GF. Rutjes FPJT. van Delft FL. Chem. Rev.  2005,  105:  775 

<A NAME="RM07110SS-2">2</A> Pang L.-J. Wang D. Zhou J. Zhang L.-H. Ye X.-S. Org. Biomol. Chem.  2009,  7:  4252 

<A NAME="RM07110SS-3">3</A> Beniazza R. Desvergnes V. Landais Y. Org. Lett.  2008,  10:  4195 

<A NAME="RM07110SS-4">4</A> Cherney RJ. Brogan JB. Mo R. Lo YC. Yang G. Miller PB. Scherle PA. Molino BF. Carter PH. Decicco CP. Bioorg. Med. Chem. Lett.  2009,  19:  597 

<A NAME="RM07110SS-5A">5a</A> Fischer EO. Fischer RD. Angew. Chem.  1960,  72:  919 

<A NAME="RM07110SS-5B">5b</A> Jones D. Pratt L. Wilkinson G. J. Chem. Soc.  1962,  4458 

<A NAME="RM07110SS-5C">5c</A> Tao C. In Encyclopedia of Reagents in Organic Synthesis   Vol. 7:  Paquette LA. John Wiley & Son; Chichester: 1995.  p.5043-5044  

<A NAME="RM07110SS-6">6</A> Sar A. Lindeman S. Donaldson WA. Org. Biomol. Chem.  2010,  8:  3908 

<A NAME="RM07110SS-7A">7a</A> Cookson RC. Gilani SSH. Stevens IDR. Tetrahedron Lett.  1962,  3:  615 

<A NAME="RM07110SS-7B">7b</A> Wichterle O. Collect. Czech. Chem. Commun.  1947,  12:  292 

<A NAME="RM07110SS-7C">7c</A> Anson CE. Hartmann S. Kelsey RD. Stephenson GR. Polyhedron  2000,  19:  569 

<A NAME="RM07110SS-7D">7d</A> Templin SS. Wallock NJ. Bennett DW. Siddiquee T. Haworth DT. Donaldson WA. J. Heterocycl. Chem.  2007,  44:  719 

<A NAME="RM07110SS-8">8</A>

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: [phone]; e-mail: [e-mail]. For the ORTEPs of (±)-7 and (±)-10 see Supporting Information.

<A NAME="RM07110SS-9A">9a</A> Cicchi S. Goti A. Brandi A. Guarna A. DeSarlo F. Tetrahedron Lett.  1990,  31:  3351 

<A NAME="RM07110SS-9B">9b</A> Ritter AR. Miller MJ. J. Org. Chem.  1994,  59:  4602 

<A NAME="RM07110SS-10A">10a</A> Kirby GW. Nazeer M. J. Chem. Soc., Perkin Trans. 1  1993,  1397 

<A NAME="RM07110SS-10B">10b</A> Miller A. Procter G. Tetrahedron Lett.  1990,  31:  1043 

<A NAME="RM07110SS-10C">10c</A> Ritter AR. Miller MJ. J. Org. Chem.  1994,  59:  4602 

<A NAME="RM07110SS-11A">11a</A> Yamamoto Y. Yamamoto H. J. Am. Chem. Soc.  2004,  126:  4128 

<A NAME="RM07110SS-11B">11b</A> Yamamoto Y. Yamamoto H. Angew. Chem. Int. Ed.  2005,  44:  7082 

<A NAME="RM07110SS-12A">12a</A> Jana CK. Studer A. Angew. Chem. Int. Ed.  2007,  46:  6542 

<A NAME="RM07110SS-12B">12b</A> Jana CK. Studer A. Chem. Eur. J.  2008,  14:  6326 

<A NAME="RM07110SS-13">13</A> Cesario C. Tardibono LP. Miller MJ. J. Org. Chem.  2009,  74:  448