tert-Butyl(2-oxo-2H-pyran-5-yl)carbamate as the First Chameleon Diene Bearing an Electron-Donating Substituent

Omar, Yasser, Santucci, Giulia and Afarinkia, Kamyar ORCID: https://orcid.org/0000-0003-2819-4364 (2022) tert-Butyl(2-oxo-2H-pyran-5-yl)carbamate as the First Chameleon Diene Bearing an Electron-Donating Substituent. Molecules.

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Abstract

The 2(H)-pyran-2-one bearing electron-donating tert-butylcarbamate (BocNH-) group at the 5- position is a “chameleon” diene and undergoes efficient Diels–Alder cycloadditions with alkene dienophiles with both electron-rich and electron-deficient substituents. Cycloadditions afford the 5-substituted bicyclic lactone cycloadducts regardless of the electronic nature of the dienophile. However, cycloadditions with electronically matched electron-deficient dienophiles proceed faster than those with electronically mismatched electron-rich dienophiles.

Item Type: Article
Keywords: Diels-Alder; cycloaddition, 2(H)-pyran-2-one; electron demand
Subjects: Natural sciences
Related URLs:
Depositing User: Kamyar Afarinkia
Date Deposited: 09 Sep 2022 12:23
Last Modified: 09 Sep 2022 12:23
URI: https://repository.uwl.ac.uk/id/eprint/9392

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