Enantioselective Organocatalytic Synthesis of δ-Lactone-Fused 4-Chromanones

Yu Ting Lai, Koppanathi Nagaraju, Ramani Gurubrahamam*, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

An organocatalytic enantioselective synthesis of δ-lactone-fused 4-chromanones was demonstrated using 1-(2-hydroxyaryl)-1,3-butanedione and α,β-unsaturated aldehydes in the presence of the Jørgensen-Hayashi catalyst. The reaction proceeded through a Michael addition/cycloketalization/hemiacetalization sequence, and the resulting hemiacetals were oxidized into the corresponding lactone derivatives in a one-pot manner. The desired fused O,O-ketal tricyclic lactone motifs containing three contiguous chiral centers were obtained in excellent chemical yields (up to 97%) and with high stereoselectivities (up to >20:1 dr and up to 95% ee). (Figure presented.).

Original languageEnglish
Pages (from-to)3846-3850
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number18
DOIs
Publication statusPublished - 2020 Sept 21

Keywords

  • 1,3-dione
  • Jørgensen-Hayashi catalyst
  • Michael addition
  • asymmetric organocatalysis
  • chromanone
  • cycloketalization
  • fused ketal
  • iminium activation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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