On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations

ABSTRACT: Detailed DFT studies provide an in-depth mechanistic understanding for the use of chiral amide-based ammonium ylides in epoxidation reactions. It is shown that the used chiral auxiliary efficiently shields one face of the ylide, which thus results in an extraordinarily high stereoselectivi...

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Detalles Bibliográficos
Autores principales: Novacek, Johanna, Robiette, Raphaël, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2016
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225234/
https://www.ncbi.nlm.nih.gov/pubmed/28127093
http://dx.doi.org/10.1007/s00706-016-1866-8
Descripción
Sumario:ABSTRACT: Detailed DFT studies provide an in-depth mechanistic understanding for the use of chiral amide-based ammonium ylides in epoxidation reactions. It is shown that the used chiral auxiliary efficiently shields one face of the ylide, which thus results in an extraordinarily high stereoselectivity giving only one trans-isomer with perfect control of the absolute configuration. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00706-016-1866-8) contains supplementary material, which is available to authorized users.

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