Chiral Brønsted acid and gold catalyzed enantioselective synthesis of 1,8-dihydroindeno[2,1-b]pyrroles

Jianwen Jin, Yichao Zhao, Ella Min Ling Sze, Prasath Kothandaraman, Philip Wai Hong Chan

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9 Citations (Scopus)

Abstract

An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Brønsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99% and enantiomeric excess (ee) values up to 99%, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).

Original languageEnglish
Pages (from-to)4744-4753
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number24
DOIs
Publication statusPublished - 21 Dec 2018

Keywords

  • asymmetric synthesis
  • chiral Brønsted acid catalysis
  • dehydrative Nazarov-type electrocyclization
  • gold catalysis
  • N-heterocyclic synthesis

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