Perreault Christian, Goudreau Sébastien R, Zimmer Lucie E, Charette André B
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Org Lett. 2008 Mar 6;10(5):689-92. doi: 10.1021/ol702414e. Epub 2008 Feb 8.
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.