2026-04-14T05:37:24Zhttps://recercat.cat/oai/request

oai:recercat.cat:2072/3506852024-12-20T19:19:16Zcom_2072_300912com_2072_4427col_2072_301309

00925njm 22002777a 4500 dc Dell Amico, Luca author Vega-Penaloza, Alberto author Cuadros, Sara author Melchiorre, Paolo author 2016-01-19 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 enantioselec- tive catalytic approach. Herein, we demonstrate how asym- metric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy-o-qui- nodimethanes 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. http://hdl.handle.net/2072/350685 https://doi.org/10.1002/anie.201509472 Enantioselective Organocatalytic Diels–Alder Trapping of Photochemically Generated Hydroxy-o-Quinodimethanes