α-Pyridylation of chiral amines via urea coupling, lithiation and rearrangement

Jonathan Clayden*, Ulrich Hennecke

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

86 Citations (Scopus)

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 languageEnglish
Pages (from-to)3567-3570
Number of pages4
JournalOrganic Letters
Volume10
Issue number16
Early online date22 Jul 2008
DOIs
Publication statusPublished - 21 Aug 2008

Fingerprint Dive into the research topics of 'α-Pyridylation of chiral amines via urea coupling, lithiation and rearrangement'. Together they form a unique fingerprint.

Cite this