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Synthesis 2011(20): 3297-3300  
DOI: 10.1055/s-0030-1260195
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of β-Aminocyclohexanones and β-Aminocyclohexanols through an Intramolecular Tandem Isomerization-Mannich Reaction as a Key Step

Hai Thuong Cao, Danielle Grée, René Grée*
Université de Rennes 1, Laboratoire Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
Fax: +33(2)23236978; e-Mail: rene.gree@univ-rennes1.fr;
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Publication History

Received 29 June 2011
Publication Date:
01 September 2011 (online)

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Abstract

New β-aminocyclohexanones and β-aminocyclohexanols, with a primary amino group, have been obtained by a short and efficient sequence involving an intramolecular tandem isomerization-Mannich reaction as the key step. This methodology takes advantage of tert-butanesulfinyl protection of the nitrogen atom.

Key words

isomerization - catalysis - nickel - carbocycles - Mannich

    References

  • For reviews on Ferrier carbocyclization, see:
  • 1a Ferrier RJ. Middleton S. Chem. Rev.  1993,  93:  2779 
    Search in Google Scholar
  • 1b Ferrier RJ. Top. Curr. Chem.  2001,  215:  277 ; and references cited therein
    Search in Google Scholar
  • 2 Mac DH. Samimeni R. Petrignet J. Srihari P. Chandrasekhar S. Yadav JS. Grée R. Chem. Commun.  2009,  31:  4717 
    Search in Google Scholar
  • For representative reviews on aminocyclitols, see:
  • 3a Chen X. Fan X. Zheng Y. Shen Y. Chem. Rev.  2003,  103:  1955 
    Search in Google Scholar
  • 3b Arjona O. Gomez AM. Lopez JC. Plumet J. Chem. Rev.  2007,  107:  1919 
    Search in Google Scholar
  • 3c Delgado A. Eur. J. Org. Chem.  2008,  3893 ; and references cited therein
  • For recent syntheses of aminocyclitol-type molecules, see:
  • 4a El Blidi L. Ahbala M. Bolte J. Lemaire M. Tetrahedron: Asymmetry  2006,  2684 
  • 4b Chakraborty C. Vyavahare VP. Puranik VC. Dhavale DD. Tetrahedron  2008,  64:  9574 
    Search in Google Scholar
  • 4c Errasti G. Koundé C. Mirguet O. Lecourt T. Micouin L. Org. Lett.  2009,  11:  2912 
    Search in Google Scholar
  • 4d Pandey G. Rajender S. Chem. Eur. J.  2011,  17:  6304 ; and references cited therein
    Search in Google Scholar
  • For intermolecular tandem isomerization-Mannich processes from allylic alcohols, see:
  • 5a Yang X.-F. Wang M. Varma RS. Li C.-J. Org. Lett.  2003,  5:  657 
    Search in Google Scholar
  • 5b Yang X.-F. Wang M. Varma RS. Li C.-J. J. Mol. Catal. A: Chem.  2004,  214:  147 
    Search in Google Scholar
  • 5c Ahlsten N. Martin-Matute B. Adv. Synth. Catal.  2009,  351:  2657 
    Search in Google Scholar
  • 5d Cao HT. Roisnel T. Grée R. Lett. Org. Chem.  2009,  6:  507 
    Search in Google Scholar
  • 5e Cao HT. Roisnel T. Valleix A. Grée R. Eur. J. Org. Chem.  2011,  3430 
  • For comprehensive reviews on the synthesis and uses of N-tert-butanesulfinamines, see:
  • 6a Ellman JA. Owens TD. Tang TP. Acc. Chem. Res.  2002,  35:  984 
    Search in Google Scholar
  • 6b Robak MT. Hernage MA. Ellman JA. Chem. Rev.  2010,  110:  3600 ; and references cited therein
    Search in Google Scholar