1239691-87-2Relevant articles and documents
On the scope of Pd-catalyzed carboamination reactions - Synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines
Jepsen, Tue Heesgaard,Larsen, Mogens,Nielsen, Mogens Br?ndsted
experimental part, p. 6133 - 6137 (2010/09/15)
The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated. Formation of a 2,4-disubstituted pyrrolidine proceeded in high yield but with a diastereoisomeric ratio of only 2:5, favoring the cis-isomer. The diastereoselectivity is hence significantly smaller than that observed previously in the formation of 2,3- and 2,5-disubstituted pyrrolidines. The yields of substituted piperidines and morpholines were lowered by competing Heck arylation reactions. Both the N-substituent and the choice of phosphine ligand for the palladium-catalyzed reaction were determining for the outcome. The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated.