Issue 13, 2024

IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Abstract

The asymmetric catalytic inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with a variety of simple olefins has been accomplished, significantly expanding the applicability of this cyclization to both cyclic hetero-dienes and dienophiles. A new type of strong Lewis acid catalyst of ferric salt enables the LUMO activation of dioxopyrrolidines via formation of cationic species, this method yields a range of bicyclic dihydropyran derivatives with exceptional outcomes, including high yields (up to 99%), diastereoselectivity (up to 99 : 1) and enantioselectivity (up to 99% ee) under mild conditions. This facile protocol was available for the late-stage modification of several bioactive molecules and transformation into macrocycle molecules as well. The origins of enantioselectivity were elucidated based on control experiments.

Graphical abstract: IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Jan 2024
Accepted
28 Feb 2024
First published
29 Feb 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 4797-4803

IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

T. Zhan, L. Zhou, Y. Zhou, B. Yang, X. Feng and X. Liu, Chem. Sci., 2024, 15, 4797 DOI: 10.1039/D4SC00078A

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