A Counterion‐Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes

An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimeri...

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Detalles Bibliográficos
Autores principales: Kiss, Emily, Campbell, Craig D., Driver, Russell W., Jolliffe, John D., Lang, Rosemary, Sergeieva, Tetiana, Okovytyy, Sergiy, Paton, Robert S., Smith, Martin D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113799/
https://www.ncbi.nlm.nih.gov/pubmed/27714921
http://dx.doi.org/10.1002/anie.201608534
Descripción
Sumario:An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimerization cascade in which size and coordination of the counterion is key.

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