Chromatographically separable rotamers of an unhindered amide

Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotame...

Descripción completa

Detalles Bibliográficos
Autores principales: Geffe, Mario, Andernach, Lars, Trapp, Oliver, Opatz, Till
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999880/
https://www.ncbi.nlm.nih.gov/pubmed/24778722
http://dx.doi.org/10.3762/bjoc.10.63
Descripción
Sumario:Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were compared to each other as well as to results obtained by DFT calculations.

Ejemplares similares