(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

Xian Huang, Waygen Thor, Xiangyu Feng, Liangliang Kang, Min Yang, Chi Sing LEE*, Yuen Kit CHENG, Shuzhong He

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

(4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4-. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.

Original languageEnglish
Pages (from-to)255-260
Number of pages6
JournalOrganic Chemistry Frontiers
Volume7
Issue number2
DOIs
Publication statusPublished - 21 Jan 2020

Scopus Subject Areas

  • Organic Chemistry

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