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Zhi-Jun Jia, Quan Zhou, Qing-Qing Zhou, Peng-Qiao Chen and Prof. Dr. Ying-Chun Chen exo-Selective Asymmetric Diels–Alder Reaction of 2,4-Dienals and Nitroalkenes by Trienamine Catalysis Angewandte Chemie International Edition 50

Version of Record online: 22 JUL 2011 | DOI: 10.1002/anie.201102013

Thumbnail image of graphical abstract

Raising the HOMO: 2,4-Dienals can react with nitroalkenes in trienamine-catalyzed asymmetric Diels–Alder reactions (see scheme). Crucial for the success is raising the HOMO energy of the diene through the introduction of appropriate substituents. The reaction exhibits unusually high enantioselectivity and exo selectivity; endo addition is possibly disfavored because of the electrostatic repulsion shown in the scheme.

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