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On the origin of cis/trans stereoselectivity in intramolecular Diels-Alder reactions of substituted pentadienyl acrylates: a comprehensive density functional study

Paddon-Row, Michael; Moran, Damian; Jones, Garth; Sherburn, Michael


A gas-phase B3LYP/6-31+G(d) study of substituent effects on the stereochemistry of both intramolecular Diels-Alder (IMDA) reactions of 9-E- and 9-Z-substituted pentadienyl acrylates and intermolecular Diels-Alder (DA) reactions between butadiene and monosubstituted alkenes and 3-substituted acrylates is reported and involves the calculation of 230 transition structures. It was found that, although exo ("anti-Alder") addition of monosubstituted ethenes to butadiene is the norm, Alder endo...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo051973q


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