Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reaction...
| Authors: | ; |
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| Format: | Article |
| Status: | Published version |
| Publication date: | 2013 |
| Country: | Argentina |
| Institution: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repository: | CONICET Digital (CONICET) |
| Language: | English |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/6052 |
| Online Access: | http://hdl.handle.net/11336/6052 |
| Access Level: | Open access |
| Keyword: | Theoretical Investigation Diels-Alder Reaction Boronates https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Summary: | The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities. |
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