Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent S(N)′-S(N)′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary

Reactions of (4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easil...

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Detalles Bibliográficos
Autores principales: Martelli, Gianluca, Marcucci, Eleonora, Orena, Mario, Rinaldi, Samuele
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255381/
https://www.ncbi.nlm.nih.gov/pubmed/19701126
http://dx.doi.org/10.3390/molecules14082824
Descripción
Sumario:Reactions of (4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easily separable [2-(3",4"-dimethyl-2"-oxo-5"-phenylimidazolidine-1-carboxamido)(aryl)methyl]acrylates 8 and 9.

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