A Brønsted base-promoted diastereoselective dimerization of azlactones

A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistr...

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Detalles Bibliográficos
Autores principales: Pinheiro, Danielle L J, Batista, Gabriel M F, de Castro, Pedro P, Flores, Leonã S, Andrade, Gustavo F S, Amarante, Giovanni W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753058/
https://www.ncbi.nlm.nih.gov/pubmed/29564003
http://dx.doi.org/10.3762/bjoc.13.264
Descripción
Sumario:A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using (1)H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.

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