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Synlett 1998; 1998(2): 206-208
DOI: 10.1055/s-1998-1589
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Stereocontrolled Addition of π-type Nucleophiles to a Bicyclic N-Acyliminium Ion. New Access to trans-2,6-Disubstituted Piperidine Substructures

Marc David* , Hamid Dhimane, Corinne Vanucci-Bacqué, Gérard Lhommet
  • *Université Pierre et Marie Curie, Laboratoire de Chimie des Hétérocycles, associé au CNRS, 4 Place Jussieu, F-75252 Paris Cedex 05, France; Fax 33 (0) 1 44 27 30 56; E-mail: lhommet@ccr.jussieu.fr
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Publication History

Publication Date:
31 December 2000 (online)

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Bicyclic N-acyliminium ion I, generated in situ by treatment of aminoether 4 with Lewis acids, smoothly reacted with π-type nucleophiles, leading exclusively to the trans adducts.

aminoether - N-acyliminium - piperidine - stereoselective - stereoelectronic