| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5269842 | Tetrahedron Letters | 2010 | 4 Pages |
Abstract
The concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied to the Diels-Alder cycloaddition between 2-alkynoic acids as dienophiles and various dienes. These [4+2] cycloadditions produce cyclohexadienyl carboxylic acids, which can be oxidized in situ to produce polysubstituted aromatic carboxylic acids. The boronic acid catalyst is suspected to provide activation by a LUMO-lowering effect of the unsaturated carboxylic acid likely via a covalent, monoacylated hemiboronic ester intermediate.
Graphical abstractA new methodology based on boronic acid catalysis of Diels-Alder cycloadditions of 2-alkynoic acids was developed.Download full-size image
Related Topics
Physical Sciences and Engineering
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Authors
Hongchao Zheng, Dennis G. Hall,