Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters

[Image: see text] The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and α-aryl-α-isocyanoacetate esters provides tricyclic compounds bearing the 3a,8b-dihydro-1H-benzofuro[2,3-c]pyrrole framework with three consecutive stereogenic centers. The reactio...

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Autores principales: Laviós, Adrian, Sanz-Marco, Amparo, Vila, Carlos, Muñoz, M. Carmen, Pedro, José R., Blay, Gonzalo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8961877/
https://www.ncbi.nlm.nih.gov/pubmed/35293212
http://dx.doi.org/10.1021/acs.orglett.2c00427
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author Laviós, Adrian
Sanz-Marco, Amparo
Vila, Carlos
Muñoz, M. Carmen
Pedro, José R.
Blay, Gonzalo
author_facet Laviós, Adrian
Sanz-Marco, Amparo
Vila, Carlos
Muñoz, M. Carmen
Pedro, José R.
Blay, Gonzalo
author_sort Laviós, Adrian
collection PubMed
description [Image: see text] The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and α-aryl-α-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.
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spelling pubmed-89618772022-03-30 Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters Laviós, Adrian Sanz-Marco, Amparo Vila, Carlos Muñoz, M. Carmen Pedro, José R. Blay, Gonzalo Org Lett [Image: see text] The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and α-aryl-α-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. American Chemical Society 2022-03-16 2022-03-25 /pmc/articles/PMC8961877/ /pubmed/35293212 http://dx.doi.org/10.1021/acs.orglett.2c00427 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Laviós, Adrian
Sanz-Marco, Amparo
Vila, Carlos
Muñoz, M. Carmen
Pedro, José R.
Blay, Gonzalo
Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title_full Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title_fullStr Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title_full_unstemmed Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title_short Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
title_sort metal-free diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and isocyanoacetate esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8961877/
https://www.ncbi.nlm.nih.gov/pubmed/35293212
http://dx.doi.org/10.1021/acs.orglett.2c00427
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