2026-04-14T03:24:20Zhttps://recercat.cat/oai/request
oai:recercat.cat:2072/3506852024-12-20T19:19:16Zcom_2072_300912com_2072_4427col_2072_301309
RECERCAT author Dell Amico, Luca author Vega-Penaloza, Alberto author Cuadros, Sara author Melchiorre, Paolo 2019-02-27T15:29:15Z2024-04-23T10:20:53Z 2019-02-27T15:29:15Z2024-04-23T10:20:53Z 2016-01-19 http://hdl.handle.net/2072/350685 https://doi.org/10.1002/anie.201509472 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. eng L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ Enantioselective Organocatalytic Diels–Alder Trapping of Photochemically Generated Hydroxy-o-Quinodimethanes info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion URL https://recercat.cat/bitstream/2072/350685/5/16_Enantioselective%20Organocatalytic%20Diels-Alder.pdf File MD5 94196a6d07ca4d35e739e49eb0b591dd 3228301 application/pdf 16_Enantioselective Organocatalytic Diels-Alder.pdf URL https://recercat.cat/bitstream/2072/350685/1/16_Enantioselective%20Organocatalytic%20Diels-Alder.pdf.txt File MD5 a9863407356d66eb7d2a2bd8a26a0188 21251 text/plain 16_Enantioselective Organocatalytic Diels-Alder.pdf.txt