Issue 6, 2024

Polyenolate-mediated reaction cascade initiated by higher-order-cycloaddition for the construction of polycarbocyclic scaffolds

Abstract

In this manuscript, the application of polyenolate chemistry for the activation of higherenes towards a higher-order-cycloaddition-initiated cascade reaction is demonstrated. This has been made possible by using alkylidenemalononitriles derived from indene-2-carbaldehydes as the higherene precursors. Their reaction with an iminium ion, generated in situ in the presence of a suitable amino catalyst, allowed for a cascade reaction involving [10 + 2]-higher-order cycloaddition followed by Michael addition and aldol condensation to proceed in a highly stereoselective fashion.

Graphical abstract: Polyenolate-mediated reaction cascade initiated by higher-order-cycloaddition for the construction of polycarbocyclic scaffolds

Supplementary files

Article information

Article type
Research Article
Submitted
12 Dec 2023
Accepted
12 Jan 2024
First published
19 Jan 2024
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 1700-1705

Polyenolate-mediated reaction cascade initiated by higher-order-cycloaddition for the construction of polycarbocyclic scaffolds

A. Cieśliński, A. Skrzyńska, A. Przydacz and Ł. Albrecht, Org. Chem. Front., 2024, 11, 1700 DOI: 10.1039/D3QO02040A

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