Abstract
(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.
Original language | English |
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Pages (from-to) | 3567-3570 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 10 |
Issue number | 16 |
Early online date | 22 Jul 2008 |
DOIs | |
Publication status | Published - 21 Aug 2008 |