To date, very few strategies have been exploited for the activation of carboxylic acids. It can be envisioned that ortho-substituted arylboronic acids could catalyze direct cycloadditions to a,�-unsaturated carboxylic acids by lowering the LUMO energy in the putative intermediate 1. Recently, we found that certain ortho-substituted arylboronic acids can catalyze Diels-Alder reactions as well as [1,3]-dipolar cycloadditions between a,�-unsaturated carboxylic acids and azides, nitrile oxides, and nitrones under mild conditions at room temperature and in excellent yields and high regioselectivities.

Boronic acid catalysis for mild and selective cycloadditions of unsaturated carboxylic acids

240th National Meeting (2010)

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