Understanding reactivity and regioselectivity in Diels-Alder reactions of a sugar-derived dienophile bearing two competing EWGs. An experimental and computational study

- The effect of an extra EWG in DA reactions of a sugar dienophile was studied.
- Conceptual DFT calculations predicted an important enhancement in the reactivity.
- This treatment failed in predicting the regiochemical preference with some dienes.
- MPW1K/6-31G* calculations correctly reproduced the experimental observations.
- The ease of pyramidalization dictates the regioselectivity.