Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates

Ling Meng, Heyang Liu, Zhenyang Lin*, Jun Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Highly efficient and straightforward access to enantioenriched five-membered ring-fused chromanones is developed via [3+2]-cycloaddition of 3-cyanochromones with Morita-Baylis-Hillman carbonates. Densely functionalized chiral cyclopenta[b]chromanones with three continuous quaternary and tertiary stereogenic carbon centers were obtained in high yields with high ee and dr (≤97% yield, 97% ee, and >20:1 dr). Moreover, density functional theory calculations have been carried out to investigate the mechanism and regio- and diastereoselectivity of the reaction.

Original languageEnglish
Pages (from-to)5890-5895
Number of pages6
JournalOrganic Letters
Volume24
Issue number32
Early online date4 Aug 2022
DOIs
Publication statusPublished - 19 Aug 2022

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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