Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

Jonathan Clayden*, Jérémy Dufour, Damian M. Grainger, Madeleine Helliwell

*Corresponding author for this work

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

100 Citations (Scopus)

Abstract

On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity.

Original languageEnglish
Pages (from-to)7488-7489
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number24
Early online date24 May 2007
DOIs
Publication statusPublished - 20 Jun 2007

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