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Synlett 1999; 1999(S1): 960-962
DOI: 10.1055/s-1999-3092
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Carba-Methylephedrine and Carba-pseudo-Methylephedrine as Tools for Probing the Role of the Nitrogen Atom of Chiral Amino Alcohols in Asymmetric Synthesis

Dominique Cahard* , Laurent Ferron, Jean-Christophe Plaquevent
  • *Université de Rouen, UPRES-A 6014 et Institut de Recherche an Chimie Organique Fine (IRCOF), 76821 Mont Saint-Aignan Cedex, France; E-mail: Jean-Christophe.Plaquevent@univ-rouen.fr
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Publication Date:
31 December 1999 (online)

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As part of our on-going program on the use of chiral alkoxides as chiral bases in asymmetric synthesis, we report that carba-ephedrine analogues of N-methylephedrines, with a simple change of bridging nitrogen for CH, served to probe the role of the nitrogen atom in the discrimination of enantiotopic protons by means of the derived alkoxides. We suggest reasons why in the pseudo ephedrine series the asymmetric induction is retained while in the ephedrine series the enantioselectivity is stronlgy affected.

chiral alkoxide - ephedrine - carba-ephedrine - enantioselective dehydrohalogenation