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Cycloadditions of Aromatic Azomethine Imines with 1,1-Cyclopropane Diesters

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journal contribution
posted on 06.03.2008, 00:00 by Christian Perreault, Sébastien R. Goudreau, Lucie E. Zimmer, André B. Charette
The cycloaddition of aromatic azomethine imines to 1,1-cyclopropane diesters was achieved using Ni(ClO4)2 as catalyst. The methodology gives access to unique tricyclic dihydroquinoline derivatives with dr up to 6.6:1. A nonconcerted mechanism is proposed on the basis of stereochemical analysis of the reaction.