Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate

Masahiro Terada, Takuto Yamanaka, Yasunori Toda

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Anionic! Novel chiral anion catalysis of the enantioselective 1,4-reduction of the 1-benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two-step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H-chromen-2-ol derivatives to generate the achiral 1-benzopyrylium ion as a reactive key intermediate.

Original languageEnglish
Pages (from-to)13658-13662
Number of pages5
JournalChemistry - A European Journal
Volume19
Issue number41
DOIs
Publication statusPublished - 2013 Oct 4

Keywords

  • Brønsted acids
  • asymmetric catalysis
  • benzopyrylium
  • enantioselective reduction
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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