Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine

Yan Cheng Liou, Yi Ru Chen, Ching Wen Hsu, Xuan Rui Huang, Heng Wei Wang, Wenwei Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A quinine-derived thiourea-catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor-donor-acceptor with salicylaldehyde-derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3-b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H-bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.

Original languageEnglish
Pages (from-to)3603-3610
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume365
Issue number21
DOIs
Publication statusPublished - 2023 Nov 7

Keywords

  • Annulation
  • Asymmetric synthesis
  • Azomethine ylides
  • Meldrum′s acid
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine'. Together they form a unique fingerprint.

Cite this