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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Detalles Bibliográficos
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:
Full Research Paper
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
Descripción
Sumario: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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