A diastereoselective intermolecular heck reaction of 1,3-dioxepins |
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| Authors: | Nasveschuk Christopher G Frein Jeffrey D Jui Nathan T Rovis Tomislav |
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| Affiliation: | Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA. |
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| Abstract: | A highly diastereoselective intermolecular Heck reaction of 1,3-dioxepins is reported. Substitution at both the 2- and 4-positions of the dioxepin directs the Pd coordination and subsequent olefin insertion to provide the trans-disubstituted adduct in good yield and high diastereoselectivity. Chemoselective Heck reaction occurs at the dioxepin alkene in the presence of other olefinic functional groups. A labeling study has been conducted which suggests that the reaction is under kinetic control. |
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