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*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

摘要

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.

原文英語
頁(從 - 到)3603-3610
頁數8
期刊Advanced Synthesis and Catalysis
365
發行號21
DOIs
出版狀態已發佈 - 2023 11月 7

ASJC Scopus subject areas

  • 催化
  • 有機化學

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