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High stereoselectivity on low temperature Diels-Alder reactions

We have found that some of the usually poor dienophiles (2-cycloenones) can undergo Diels-Alder reaction at -78°C with unusually high stereoselectivity in the presence of niobium pentachloride as a Lewis acid catalyst. A remarkable difference in reaction rates for unsubstituted and α- or β-methyl su...

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Autores principales: da Silva Filho, Luiz Carlos, Lacerda Júnior, Valdemar, Constantino, Mauricio Gomes, da Silva, Gil Valdo José, Invernize, Paulo Roberto
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2005
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399462/
https://www.ncbi.nlm.nih.gov/pubmed/16542029
http://dx.doi.org/10.1186/1860-5397-1-14
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author da Silva Filho, Luiz Carlos
Lacerda Júnior, Valdemar
Constantino, Mauricio Gomes
da Silva, Gil Valdo José
Invernize, Paulo Roberto
author_facet da Silva Filho, Luiz Carlos
Lacerda Júnior, Valdemar
Constantino, Mauricio Gomes
da Silva, Gil Valdo José
Invernize, Paulo Roberto
author_sort da Silva Filho, Luiz Carlos
collection PubMed
description We have found that some of the usually poor dienophiles (2-cycloenones) can undergo Diels-Alder reaction at -78°C with unusually high stereoselectivity in the presence of niobium pentachloride as a Lewis acid catalyst. A remarkable difference in reaction rates for unsubstituted and α- or β-methyl substituted 2-cycloenones was also observed.
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spelling pubmed-13994622006-03-13 High stereoselectivity on low temperature Diels-Alder reactions da Silva Filho, Luiz Carlos Lacerda Júnior, Valdemar Constantino, Mauricio Gomes da Silva, Gil Valdo José Invernize, Paulo Roberto Beilstein J Org Chem Full Research Paper We have found that some of the usually poor dienophiles (2-cycloenones) can undergo Diels-Alder reaction at -78°C with unusually high stereoselectivity in the presence of niobium pentachloride as a Lewis acid catalyst. A remarkable difference in reaction rates for unsubstituted and α- or β-methyl substituted 2-cycloenones was also observed. Beilstein-Institut 2005-12-09 /pmc/articles/PMC1399462/ /pubmed/16542029 http://dx.doi.org/10.1186/1860-5397-1-14 Text en Copyright © 2005, da Silva Filho et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
da Silva Filho, Luiz Carlos
Lacerda Júnior, Valdemar
Constantino, Mauricio Gomes
da Silva, Gil Valdo José
Invernize, Paulo Roberto
High stereoselectivity on low temperature Diels-Alder reactions
title High stereoselectivity on low temperature Diels-Alder reactions
title_full High stereoselectivity on low temperature Diels-Alder reactions
title_fullStr High stereoselectivity on low temperature Diels-Alder reactions
title_full_unstemmed High stereoselectivity on low temperature Diels-Alder reactions
title_short High stereoselectivity on low temperature Diels-Alder reactions
title_sort high stereoselectivity on low temperature diels-alder reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399462/
https://www.ncbi.nlm.nih.gov/pubmed/16542029
http://dx.doi.org/10.1186/1860-5397-1-14
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