On the origin of cis/trans stereoselectivity in intramolecular Diels-Alder reactions of substituted pentadienyl acrylates: a comprehensive density functional study
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Paddon-Row, Michael; Moran, Damian; Jones, Garth; Sherburn, Michael
Description
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]
Collections | ANU Research Publications |
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Date published: | 2005 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/73941 |
Source: | Journal of Organic Chemistry |
DOI: | 10.1021/jo051973q |
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