Asymmetric Access to Structurally Complex 1-Tetralols through Diels-Alder Cycloadditions of Photogenerated Hydroxy-o-quinodimethanes and Acrylates.

Photoenolization/Diels-Alder (PEDA) reactions provide a rapid approach to highly substituted 1-tetralols. Herein, we report a PEDA strategy using activated acrylate-based dienophiles for the synthesis of densely functionalized 1-tetralols with high diastereoselectivity. Isatin-derived acrylates enable access to spirocyclic architectures, while chiral auxiliary-based acrylates allow an asymmetric variant, providing enantioenriched 1-tetralol derivatives with efficient stereocontrol.