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Controlling cis/trans -selectivity in intramolecular Diels-Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes

Pearson, Emma; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael

Description

Predictions from DFT (B3LYP/6-31 G(d))-computed stereoisomer product distributions for intramolecular Diels-Alder (IMDA) reactions have been successfully replicated in the laboratory. Benzo-tethered hexadienyl acrylates generally undergo moderately trans-selective IMDA reactions which, as suggested by DFT calculation, arise from two opposing transition structure (TS) features: stabilising secondary orbital interactions, which are stronger in the cis-TSs, and stabilising π-conjugative...[Show more]

CollectionsANU Research Publications
Date published: 2008
Type: Journal article
URI: http://hdl.handle.net/1885/49781
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b716910h

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