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Synlett 2011(13): 1816-1820  
DOI: 10.1055/s-0030-1260964
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Allyl and Benzyl Dance under Basic Conditions

Laurent El Kaim*, Laurence Grimaud*, Srinivas Reddy Purumandla
Laboratoire Chimie et Procédés, UMR 7652, Ecole Polytechnique-ENSTA-CNRS, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45528322; e-Mail: laurent.elkaim@ensta.fr; e-Mail: grimaud@dcso.polytechnique.fr;
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Publication History

Received 9 May 2011
Publication Date:
21 July 2011 (online)

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Abstract

Ugi-Smiles adducts formed from allyl (propargyl or benzyl) amine rearrange under basic condition with an allyl migration between two nitrogen atoms. The shift is reversible and may be controlled by the strength of the base used in the reaction.

Key words

Ugi-Smiles - isocyanide - multicomponent couplings - allyl - benzyl - propargyl - migration

    References and Notes

  • 1a El Kaïm L. Grimaud L. Oble J. Angew. Chem. Int. Ed.  2005,  117:  7961 
    Google Scholar
  • 1b El Kaïm L. Gizolme M. Grimaud L. Oble J. J. Org. Chem.  2007,  72:  4169 
    Google Scholar
  • 1c Barthelon A. El Kaim L. Gizolme M. Eur. J. Org. Chem.  2008,  5974 
    Google Scholar
  • 2a El Kaim L. Gizolme M. Grimaud L. Oble J. J. Org. Chem.  2007,  72:  5835 
    Google Scholar
  • 2b Oble J. El Kaim L. Gizzi M. Grimaud L. Heterocycles  2007,  73:  503 
    Google Scholar
  • 2c El Kaim L. Grimaud L. Gizzi M. Org. Lett.  2008,  10:  3417 
    Google Scholar
  • 2d Coffinier D. El Kaim L. Grimaud L. Org. Lett.  2009,  11:  995 
    Google Scholar
  • 2e Barthelon A. Legoff X.-F. El Kaim L. Grimaud L. Synlett  2010,  153 
    Google Scholar
  • 2f El Kaïm L. Grimaud L. Mol. Diversity  2010,  14:  855 
    Google Scholar
  • 2g El Kaim L. Grimaud L. Wagschal S. J. Org. Chem.  2010,  75:  5343 
    Google Scholar
  • 2h El Kaim L. Grimaud L. Wagschal S. Chem. Commun.  2011,  47:  1887 
    Google Scholar
  • 3a El Kaim L. Gamez-Montaño R. Grimaud L. Ibarra-Rivera T. Chem. Commun.  2008,  1350 
    Google Scholar
  • 3b El Kaim L. Grimaud L. Legoff X.-F. Schiltz A. Org. Lett.  2011,  13:  534 
    Google Scholar
  • 4a El Kaim L. Grimaud L. Wagschal S. J. Org. Chem.  2010,  75:  5343 
    Google Scholar
  • For similar synthetic strategies with classical Ugi adducts, see:
  • 4b Marcaccini S. Pepino R. Pozo MC. Tetrahedron Lett.  2001,  42:  2727 
    Google Scholar
  • 4c Bossio R. Marcos CF. Marcaccini S. Pepino R. Heterocycles  1997,  45:  1589 
    Google Scholar
  • 4d Bossio R. Marcos CF. Marcaccini S. Pepino R. Synthesis  1997,  1389 
    Google Scholar
  • 5 This term has been mainly used for the ‘halogen-dance reaction’. It involves migration of halogen atoms when aryl derivatives are treated under basic conditions. See: Bunnett JF. Acc. Chem. Res.  1972,  5:  139 
    CrossrefPubMedGoogle Scholar
  • 5For a more recent use, see:
  • 5 Stanetty P. Schnürch M. Mereiter K. Mihovilovic MD. J. Org. Chem.  2005,  70:  567 
    CrossrefPubMedGoogle Scholar