Abstract
| - A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition useful in the synthesis ofchromanes is described. The reaction relies on the use of a chiral auxiliary on the nitrone partner.Key to the success of the reaction is the choice of auxiliary and the choice of Lewis acid catalyst.Utilizing an auxiliary with a pendant coordinating group, and Zn(OTf)2 as the Lewis acid,diastereoselectivities up to 22:1 could be achieved.
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