Issue 23, 2023

Efficient synthesis of fully renewable, furfural-derived building blocks via formal Diels–Alder cycloaddition of atypical addends

Abstract

Diels–Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack of reactivity of the most readily available furans, i.e. the furfural derivatives. Herein we describe the remarkably-facile intramolecular DA reaction of allyl acetals of different furfurals to efficiently afford formal DA adducts with the atypical, unreactive dienophile allyl alcohol. Our methodology gives access to unprecedented oxanorbornene derivatives in high chemo-, regio- and stereoselectivity, which can be readily diversified into valuable products. This offers the potential of scalable production of renewable chemical building blocks from cheap, bioderived platform molecules.

Graphical abstract: Efficient synthesis of fully renewable, furfural-derived building blocks via formal Diels–Alder cycloaddition of atypical addends

Supplementary files

Article information

Article type
Paper
Submitted
30 Jun 2023
Accepted
30 Aug 2023
First published
31 Aug 2023
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2023,25, 9689-9694

Efficient synthesis of fully renewable, furfural-derived building blocks via formal Diels–Alder cycloaddition of atypical addends

R. C. Cioc, E. Harsevoort, M. Lutz and P. C. A. Bruijnincx, Green Chem., 2023, 25, 9689 DOI: 10.1039/D3GC02357E

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