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Stereocontrol of the Intramolecular Diels-Alder Reaction by Internal Hydrogen Bonding

Cayzer, Tory; Paddon-Row, Michael; Sherburn, Michael


A novel approach for exo/endo stereocontrol of intramolecular Diels-Alder reactions is described. Substrates carrying a hydroxymethyl group attached to the diene and an ester group attached to the dienophile participate in hydrogen bonding in the transition state. This non-covalent interaction causes either a significant enhancement or diminution in the observed kinetic endo/exo product ratio. Thus, the parent pentadienyl maleate 12 undergoes intramolecular Diels-Alder reaction to give an...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
Source: European Journal of Organic Chemistry
DOI: 10.1002/ejoc.200300414


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