Jump to main content
Jump to site search

Issue 2, 2020
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
06 Nov 2019
Accepted
06 Dec 2019
First published
09 Dec 2019

Org. Chem. Front., 2020,7, 255-260
Article type
Research Article

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

X. Huang, W. Thor, X. Feng, L. Kang, M. Yang, C. Lee, Y. Cheng and S. He, Org. Chem. Front., 2020, 7, 255
DOI: 10.1039/C9QO01349K

Social activity

Search articles by author

Spotlight

Advertisements