Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives

Jonathan Clayden*, Hazel Turner

*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

Atropisomeric N-methyl-N,N′-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 °C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity.

Original languageEnglish
Pages (from-to)3216-3219
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number26
Early online date8 Feb 2009
DOIs
Publication statusPublished - 1 Jul 2009

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