Enantioselective synthesis of atropisomeric amides by dynamic resolution: Thermodynamic control with a proline-derived diamine resolving agent

Jonathan Clayden*, Lai Wah Lai

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

87 Citations (Scopus)

Abstract

By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5% ee in 70-80% overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).

Original languageEnglish
Pages (from-to)2556-2558
Number of pages3
JournalAngewandte Chemie - International Edition
Volume38
Issue number17
DOIs
Publication statusPublished - 3 Sep 1999

Keywords

  • Amides
  • Asymmetric synthesis
  • Atropisomerism
  • Dynamic resolution

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