Synthesis of chromeno[4,3-b]pyrrolidines from azomethine ylides and vinyl para-quinone methides via (3 + 2) cycloaddition/oxa-1,6-addition

Pei Shan Wu, Yan Cheng Liou, Gangababu Marri, Yi Ru Chen, Jia Rong Wu, Wenwei Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient synthesis of chromeno[4,3-b]pyrrolidines has been successfully developed. This strategy involves a base-catalyzed reaction of p-VQMs and o-hydroxy azomethine ylides via (3 + 2) cycloaddition/oxa-1,6-addition reaction sequence. The reaction condition is mild, and a series of chromeno[4,3-b]pyrrolidines were obtained in 49-95% yields with excellent diastereoselectivity (dr > 20:1).

Original languageEnglish
Pages (from-to)2136-2146
Number of pages11
JournalJournal of the Chinese Chemical Society
Volume70
Issue number12
DOIs
Publication statusPublished - 2023 Dec

Keywords

  • azomethine ylides
  • cycloaddition
  • vinyl para-quinone methide

ASJC Scopus subject areas

  • General Chemistry

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