Enantioselective N-Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut–Currier Reaction

Song Bae, Changhe Zhang, Rachel M. Gillard, David W. Lupton

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

Abstract

While the enantioselective Rauhut–Currier reaction is established with bis(enone) substrates, it is yet to be reported with less electrophilic bis(enoate) substrates. By exploiting high-nucleophilicity N-heterocyclic carbenes, it is possible to achieve Rauhut–Currier reactions with these substrates. The reaction is demonstrated with a range of intramolecular reactions (20 examples) and six esterification/RC reaction cascades, which all proceed with high enantioselectivity (most >93:7 er).

Original languageEnglish
Pages (from-to)13370-13374
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number38
DOIs
Publication statusPublished - 16 Sep 2019

Keywords

  • bis(enoate)s
  • coumarins
  • enantioselective catalysis
  • N-heterocyclic carbenes
  • Rauhut–Currier reaction

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