Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1782126990141161472 |
---|---|
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. |
format | Text |
id | pubmed-1399462 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2005 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT dasilvafilholuizcarlos highstereoselectivityonlowtemperaturedielsalderreactions AT lacerdajuniorvaldemar highstereoselectivityonlowtemperaturedielsalderreactions AT constantinomauriciogomes highstereoselectivityonlowtemperaturedielsalderreactions AT dasilvagilvaldojose highstereoselectivityonlowtemperaturedielsalderreactions AT invernizepauloroberto highstereoselectivityonlowtemperaturedielsalderreactions |