Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocataly...

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Autores principales: Castán, Alejandro, Badorrey, Ramón, Gálvez, José A, Díaz-de-Villegas, María D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5389197/
https://www.ncbi.nlm.nih.gov/pubmed/28487754
http://dx.doi.org/10.3762/bjoc.13.59
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author Castán, Alejandro
Badorrey, Ramón
Gálvez, José A
Díaz-de-Villegas, María D
author_facet Castán, Alejandro
Badorrey, Ramón
Gálvez, José A
Díaz-de-Villegas, María D
author_sort Castán, Alejandro
collection PubMed
description New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.
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spelling pubmed-53891972017-05-09 Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins Castán, Alejandro Badorrey, Ramón Gálvez, José A Díaz-de-Villegas, María D Beilstein J Org Chem Full Research Paper New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved. Beilstein-Institut 2017-03-27 /pmc/articles/PMC5389197/ /pubmed/28487754 http://dx.doi.org/10.3762/bjoc.13.59 Text en Copyright © 2017, Castán et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Castán, Alejandro
Badorrey, Ramón
Gálvez, José A
Díaz-de-Villegas, María D
Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title_full Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title_fullStr Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title_full_unstemmed Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title_short Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
title_sort synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric michael addition of aldehydes to nitroolefins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5389197/
https://www.ncbi.nlm.nih.gov/pubmed/28487754
http://dx.doi.org/10.3762/bjoc.13.59
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