New aspects of catalytic intramolecular C-H amination: unexpected formation of a seven-membered ring in nitrogen-containing systems.
The first example of the formation of a seven-membered ring by way of intramolecular-catalyzed amination of saturated C-H bonds is reported (Du Bois reaction). The influence of various structural parameters was studied, and it was shown that the unexpected regioselectivity observed in nitrogen-containing systems could be rationalized by conformational factors. These results open the way to innovative strategies for the general synthesis of polyfunctionalized piperidines.
Toumieux
Sylvestre
S
ICOA, UMR 6005 CNRS/Université d'Orléans, rue de Chartres, BP 6759, 45067 Orléans, France.
Compain
Philippe
P
Martin
Olivier R
OR
Selkti
Mohamed
M
D000586:Amination; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D008958:Models, Molecular; D009584:Nitrogen / Q000737:chemistry*
D002244:Carbon; D006859:Hydrogen; D009584:Nitrogen