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Intramolecular Carbolithiation of N-Allyl-ynamides: an Efficient Entry to 1,4-Dihydropyridines and Pyridines - Application to a Formal Synthesis of Sarizotan

par gati, Wafa;Rammah, M. Mohamed;Rammah, B. Mohamed;Evano, Gwilherm
Référence Beilstein Journal of Organic Chemistry, 8, page (2214-2222)
Publication Publié, 2012

Article révisé par les pairs

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Résumé :

We have developed a general synthesis of polysubstituted 1,4-dihydropyridines and pyridines based on a highly regioselective lithiation/6-endo-dig intramolecular carbolithiation from readily available N-allyl-ynamides. This reaction, which has been successfully applied to the formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates the synthetic efficiency of carbometallation reactions.