1042947-64-7Relevant academic research and scientific papers
α-Pyridylation of chiral amines via urea coupling, lithiation and rearrangement
Clayden, Jonathan,Hennecke, Ulrich
, p. 3567 - 3570 (2008)
(Chemical Equation Presented) 2-, 3- and 4-Bromopyridine, along with other brominated electron-deficient arenes, undergo palladium-catalyzed coupling with ureas of structure RNMeCONHMe. Where R is a chiral, α-substituted benzyl group, treatment with LDA leads to a benzylic organolithium which undergoes rearrangement with stereospecific and regiospecific transfer of the pyridyl group, generating a quaternary stereogenic center with high enantioselectivity. Alcoholysis of the urea under neutral conditions reveals the pyridyl amine.
