We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Enantioselective Organocatalytic Diels-Alder Trapping of Photochemically Generated Hydroxy- o-Quinodimethanes.
- Authors
Dell'Amico, Luca; Vega‐Peñaloza, Alberto; Cuadros, Sara; Melchiorre, Paolo
- Abstract
The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy- o-quinodimethanes with high stereoselectivity. We used a chiral organic catalyst, derived from natural cinchona alkaloids, to activate maleimides toward highly stereoselective Diels-Alder reactions. An unconventional mechanism of stereocontrol is operative, wherein the organocatalyst is actively involved in both the photochemical pathway, by leveraging the formation of the reactive photoenol, and the stereoselectivity-defining event.
- Subjects
QUINODIMETHANE; ORGANOCATALYSIS; DIELS-Alder reaction; ENOLIZATION; ENANTIOSELECTIVE catalysis
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 10, p3313
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201509472