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Paper | Regular issue | Vol 83, No. 9, 2011, pp.2011-2039
Published online, 15th July, 2011
DOI: 10.3987/COM-11-12249
Ready Available Chiral Azapyridinomacrocycles N-Oxides; First Results as Lewis Base Catalysts in Asymmetric Allylation of p-Nitrobenzaldehyde

Maité Sylla-Iyarreta Veitía,* Mounia Joudat, Mathieu Wagner, Annie Falguières, Alain Guy, and Clotilde Ferroud*

*Laboratory of Chemical and Pharmaceutical Transformations, ERL 3193 CNRS, ESPCI ParisTech, Cnam, 2 rue Conté 75003 Paris, France

Abstract

We report here the straightforward synthesis of the first series of enantiomerically pure azapyridinomacrocycles N-oxides containing a cyclohexyl chiral moiety. These compounds were readily obtained in good overall yields by a convergent synthesis using natural amino acids as starting building blocks and macrocyclisation as the key step. This method is rapid, efficient and suitable for the introduction of various substituents at the macrocyclic skeleton. Finally, the compounds were tested as organocatalysts for the enantioselective allylation of p-nitrobenzaldehyde with allyltrichlorosilane.