Author: Juliana G. Pereira
Co-Authors: João M. J. M. Ravasco, João R. Vale, Fausto Queda and Rafael F. A. Gomes
The Diels–Alder (DA) reaction of biomass derived furans is an emerging technology for the preparation of
new molecular entities and “drop-in” commodity chemicals. In this work, we address the challenge of the
direct use of electron-poor furanic platforms as dienes through the use of an unexplored chitin derived
furan, 3-acetamido-5-acetylfuran (3A5AF). The 3-acetamido group promoted a remarkable increase in
the kinetics of the DA reaction, allowing for the preparation of 7-oxanorbornenes (7-ONBs) at 50 °C.
Partial hydrolysis of enamide to hemi-acylaminals was possible upon fine-tuning of the reaction conditions, disabling retro-DA processes. Finally, the DA reaction of the reduced form of 3A5AF allowed quantitative formation of 7-ONBs under aqueous conditions after 10 minutes. Certainly, these are the first steps for expanding the toolbox of chitin derived 3A5AF as a diene.