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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

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