N,N′-diarylureas: A new family of atropisomers exhibiting highly diastereoselective reactivity

Jonathan Clayden*, Hazel Turner, Madeleine Helliwell, Elizabeth Moir

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

35 Citations (Scopus)

Abstract

(Chemical Equation Presented) 2,6-Disubstituted N-aryl ureas rotate slowly about their Ar-N bonds and can exist as separable atropisomers. They also react remarkably diastereoselectively, with the urea axis controlling new stereogenic centers with high fidelity in a variety of nucleophilic and electrophilic addition reactions. The sense of diastereoselectivity in lateral lithiation-electrophilic quench reactions is electrophile-dependent and appears to be the result of stereospecific reaction with one of two interconvertible diastereoisomeric organolithiums.

Original languageEnglish
Pages (from-to)4415-4423
Number of pages9
JournalJournal of Organic Chemistry
Volume73
Issue number12
Early online date10 Apr 2008
DOIs
Publication statusPublished - 20 Jun 2008

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