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Synlett 2008(15): 2253-2256  
DOI: 10.1055/s-2008-1078014
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Probing the Amino-End Reactivity of Sulfonimidamides

Stéphane Azzaro, Louis Fensterbank*, Emmanuel Lacôte*, Max Malacria*
Laboratoire de Chimie Organique (UMR CNRS 7611), Institut de Chimie Moléculaire (FR 2769), Université Pierre et Marie Curie-Paris 6, C. 229, 4 Place Jussieu, 75005 Paris, France
Fax: +33(1)44277360; e-Mail: louis.fensterbank@upmc.fr; e-Mail: emmanuel.lacote@upmc.fr; e-Mail: max.malacria@upmc.fr.;
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Publication History

Received 15 May 2008
Publication Date:
31 July 2008 (online)

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Abstract

The amino terminus of sulfonimidamides was functionalized through a Mitsunobu reaction. The new sulfonimidamides were engaged in oxidative reactions to provide N-heterocycles.

Key words

aminations - diastereoselectivity - iodine - Mitsunobu reaction - sulfur

    References

  • 1a Levchenko ES. Derkach NY. Kirsanov AV. Zh. Obshch. Khim.  1960,  30:  1971 
    Google Scholar
  • 1b Johnson CR. Jonsson EU. Bacon CC. J. Org. Chem.  1979,  44:  2055 
    Google Scholar
  • 2a Toth JE. Grindey GB. Ehlhardt WJ. Ray JE. Boder GB. Bewley JR. Klingerman KK. Gates SB. Rinzel SM. Schultz RM. Weir LC. Worzalla JF.
    J. Med. Chem.  1997,  40:  1018 
    Google Scholar
  • 2b Worch C. Bolm C. Synthesis  2007,  1355 
    Google Scholar
  • 3a Espino CG. Du Bois J. Rhodium(II)-Catalyzed Oxidative Amination, In Modern Rhodium-Catalyzed Organic Reactions   Evans PA. Wiley-VCH; Weinheim: 2005.  p.379-416  
    Google Scholar
  • 3b Dauban P. Dodd RH. Synlett  2003,  1571 
    Google Scholar
  • 4a Fiori KW. Du Bois J. J. Am. Chem. Soc.  2007,  129:  562 
    Google Scholar
  • 4b Guthikonda K. Du Bois J. J. Am. Chem. Soc.  2002,  124:  13672 
    Google Scholar
  • 4c Espino CG. Wehn PM. Chow J. Du Bois J. J. Am. Chem. Soc.  2001,  123:  6935 
    Google Scholar
  • 5a Carta P. Puljic N. Robert C. Dhimane A.-L. Fensterbank L. Lacôte E. Malacria M. Org. Lett.  2007,  9:  1061 
    Google Scholar
  • 5b Coulomb J. Certal V. Fensterbank L. Lacôte E. Malacria M. Angew. Chem. Int. Ed.  2006,  45:  633 
    Google Scholar
  • 5c Leca D. Song K. Albert M. Grangeio Gonçalves M. Fensterbank L. Lacôte E. Malacria M. Synthesis  2005,  1405 
    Google Scholar
  • 5d Leca D. Song K. Amatore M. Fensterbank L. Lacôte E. Malacria M. Chem. Eur. J.  2004,  10:  906 
    Google Scholar
  • 5e Brebion F. Delouvrié B. Nájera F. Fensterbank L. Malacria M. Vaissermann J. Angew. Chem. Int. Ed.  2003,  42:  5342 
    Google Scholar
  • 5f Lacôte E. Amatore M. Fensterbank L. Malacria M. Synlett  2002,  116 
    Google Scholar
  • 5g Lacôte E. Delouvrié B. Fensterbank L. Malacria M. Angew. Chem. Int. Ed.  1998,  37:  2116 
    Google Scholar
  • 6 Leca D. Toussaint A. Mareau C. Fensterbank L. Lacôte E. Malacria M. Org. Lett.  2004,  6:  3573 
    CrossrefPubMedGoogle Scholar
  • 7a Fruit C. Robert-Peillard F. Bernardinelli G. Müller P. Dodd RH. Dauban P. Tetrahedron: Asymmetry  2005,  16:  3484 
    Google Scholar
  • 7b Di Chenna PH. Robert-Peillard F. Dauban P. Dodd RH. Org. Lett.  2004,  6:  4503 
    Google Scholar
  • 8a Liang C. Collet F. Robert-Peillard F. Müller P. Dodd RH. Dauban P. J. Am. Chem. Soc.  2008,  130:  343 
    Google Scholar
  • 8b Liang C. Robert-Peillard F. Fruit C. Müller P. Dodd RH. Dauban P. Angew. Chem. Int. Ed.  2006,  45:  4641 
    Google Scholar
  • 9a Arencibia MT. Freire R. Perales A. Rodriguez MS. Suarez E. J. Chem. Soc., Perkin Trans. 1  1991,  3349 
    Google Scholar
  • 9b Togo H. Hoshina Y. Muraki T. Nakayama H. Yokoyama M. J. Org. Chem.  1998,  63:  5193 
    Google Scholar
  • 10a Morino Y. Hidaka I. Oderaotoshi Y. Komatsu M. Minakata S. Tetrahedron  2006,  62:  12247 
    Google Scholar
  • For related DIB-mediated oxidation of sulfonamides, see:
  • 10b Lu H. Chen Q. Li C. J. Org. Chem.  2007,  72:  2564 
    Google Scholar