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Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels-Alder Reaction Employing Two Dienophiles

Muhammad Saeed Akhtar and Yong Rok Lee*

*School of Chemical Engineering, Yeungnam University, Gyeongsan 38541, Republic of Korea, Email:

M. S. Akhthar, Y. R. Lee, J. Org. Chem., 2020, 85, 15129-15138.

DOI: 10.1021/acs.joc.0c01991


L-proline catalyzes a reaction between α,β-unsaturated aldehydes and maleimides to provide biologically and pharmaceutically important phthalimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides.

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proposed reaction pathway

Key Words

Diels-Alder reaction, organocatalysis, phthalimides, air

ID: J42-Y2020