Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.