Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration

Daniel J. Tetlow, Ulrich Hennecke, James Raftery, Michael J. Waring, David S. Clarke, Jonathan Clayden*

*Corresponding author for this work

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

41 Citations (Scopus)

Abstract

On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.

Original languageEnglish
Pages (from-to)5442-5445
Number of pages4
JournalOrganic Letters
Volume12
Issue number23
Early online date9 Nov 2010
DOIs
Publication statusPublished - 3 Dec 2010

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