Enantioselective Organocatalytic Diels–Alder Trapping of Photochemically Generated Hydroxy‐ o ‐Quinodimethanes

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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Enantioselective Organocatalytic Diels–Alder Trapping of Photochemically Generated Hydroxy‐ o ‐Quinodimethanes ; volume:128 ; number:10 ; year:2016 ; pages:3374-3378 ; extent:5 ; Angewandte Chemie ; 128, Heft 10 (2016), 3374-3378 (gesamt 5)

Contributors, Places and Time

• Creator: Dell'Amico, Luca ; Vega‐Peñaloza, Alberto ; Cuadros, Sara ; Melchiorre, Paolo

Further information

• DOI: 10.1002/ange.201509472
• URN: urn:nbn:de:101:1-2022101008524623787141
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:38 AM CEST