1613408-72-2Relevant academic research and scientific papers
Directed functionalization of 1,2-dihydropyridines: Stereoselective synthesis of 2,6-disubstituted piperidines
Pelletier, Guillaume,Constantineau-Forget, Léa,Charette, André B.
, p. 6883 - 6885 (2014/06/23)
A practical and highly stereoselective approach to access 2,6-disubstituted piperidines using an amidine auxiliary is reported. Following the diastereoselective addition of Grignard reagents at the 2-position of an activated pyridinium salt, the amidine group directs a regioselective metalation at the 6-position, enabling further functionalization. A subsequent electrophilic quench or a Negishi cross-coupling could be performed, resulting in 2,6-disubstituted dihydropyridines. These were reduced to the saturated piperidine rings with high diastereoselectivity. the Partner Organisations 2014.
