Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines

[Image: see text] A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affordin...

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Autores principales: Carceller-Ferrer, Laura, Vila, Carlos, Blay, Gonzalo, Muñoz, M. Carmen, Pedro, José R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491163/
https://www.ncbi.nlm.nih.gov/pubmed/34553948
http://dx.doi.org/10.1021/acs.orglett.1c02571
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author Carceller-Ferrer, Laura
Vila, Carlos
Blay, Gonzalo
Muñoz, M. Carmen
Pedro, José R.
author_facet Carceller-Ferrer, Laura
Vila, Carlos
Blay, Gonzalo
Muñoz, M. Carmen
Pedro, José R.
author_sort Carceller-Ferrer, Laura
collection PubMed
description [Image: see text] A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affording a range of aminooxindole-pyrazolone adducts (24 examples) with excellent outcomes: up to 98% yield with complete diastereoselectivity and excellent enantioselectivity (up to 99% ee). Additionally, different synthetic transformations were performed with the chiral pyrazolone-oxindole adducts.
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spelling pubmed-84911632021-10-05 Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines Carceller-Ferrer, Laura Vila, Carlos Blay, Gonzalo Muñoz, M. Carmen Pedro, José R. Org Lett [Image: see text] A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affording a range of aminooxindole-pyrazolone adducts (24 examples) with excellent outcomes: up to 98% yield with complete diastereoselectivity and excellent enantioselectivity (up to 99% ee). Additionally, different synthetic transformations were performed with the chiral pyrazolone-oxindole adducts. American Chemical Society 2021-09-23 2021-10-01 /pmc/articles/PMC8491163/ /pubmed/34553948 http://dx.doi.org/10.1021/acs.orglett.1c02571 Text en © 2021 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 Carceller-Ferrer, Laura
Vila, Carlos
Blay, Gonzalo
Muñoz, M. Carmen
Pedro, José R.
Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title_full Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title_fullStr Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title_full_unstemmed Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title_short Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
title_sort catalytic diastereo- and enantioselective vinylogous mannich reaction of alkylidenepyrazolones to isatin-derived ketimines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491163/
https://www.ncbi.nlm.nih.gov/pubmed/34553948
http://dx.doi.org/10.1021/acs.orglett.1c02571
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