Laviós, A.; Sanz-Marco, A.; Vila, C.; Muñoz Roca, MDC.; Pedro, JR.; Blay, G. (2022). Metal-Free Diastereo- and Enantioselective Dearomative Formal [3+2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters. Organic Letters. 24(11):2149-2154. https://doi.org/10.1021/acs.orglett.2c00427
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/198425
Title:
|
Metal-Free Diastereo- and Enantioselective Dearomative Formal [3+2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
|
Author:
|
Laviós, Adrian
Sanz-Marco, Amparo
Vila, Carlos
Muñoz Roca, María Del Carmen
Pedro, José R.
Blay, Gonzalo
|
UPV Unit:
|
Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny
|
Issued date:
|
|
Abstract:
|
[EN] The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and alpha-aryl-alpha isocyanoacetate esters provides tricyclic compounds bearing the 3a,8b-dihydro-1H-benzofuro[2,3-c]pyrrole ...[+]
[EN] The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and alpha-aryl-alpha isocyanoacetate esters provides tricyclic compounds bearing the 3a,8b-dihydro-1H-benzofuro[2,3-c]pyrrole framework with three consecutive stereogenic centers. The reaction was enabled by a cupreine-ether organocatalyst. The reaction products were obtained with almost full diastereoselectivity and with excellent enantiomeric excesses for a number of substituted 2-nitrobenzofurans and isocyanoacetates.
[-]
|
Copyrigths:
|
Reconocimiento (by)
|
Source:
|
Organic Letters. (issn:
1523-7060
)
|
DOI:
|
10.1021/acs.orglett.2c00427
|
Publisher:
|
American Chemical Society
|
Publisher version:
|
https://doi.org/10.1021/acs.orglett.2c00427
|
Project ID:
|
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-116944GB-I00/ES/ESTRATEGIAS CATALITICAS ASIMETRICAS PARA LA SINTESIS DE NUEVAS ENTIDADES QUIMICAS QUIRALES CON POTENCIAL INTERES FARMACOLOGICO/
info:eu-repo/grantAgreement/MCIU//RYC-2016-20187//Ayudas para contratos Ramón y Cajal/
info:eu-repo/grantAgreement/MCIU//FPU18%2F03038//Ayudas para la Formación del Profesorado Universitario/
|
Thanks:
|
We acknowledge grant PID2020-116944GB-100 funded by MCIN/AEI/10.13039/501100011033 and by the "European Union Next Generation EU/PRTR", grant RyC-2016-20187 funded by MCIN/AEI/10.13039/501100011033 and by "ESF Investing ...[+]
We acknowledge grant PID2020-116944GB-100 funded by MCIN/AEI/10.13039/501100011033 and by the "European Union Next Generation EU/PRTR", grant RyC-2016-20187 funded by MCIN/AEI/10.13039/501100011033 and by "ESF Investing in your future" to C.V., and grant FPU18/03038 funded by MEC to A.L. We acknowledge access to the NMR, MS, and X-ray facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV. Dedicated to Professor Joan Bosch, Universitat de Barcelona, on the occasion of his 75th birthday.
[-]
|
Type:
|
Artículo
|