Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement

Employing iPrMgCl as an advanced base instead of lithium hexamethyldisilazane (LHMDS) resulted in dramatic improvements in aza-Claisen rearrangement. This advance is considered responsible for the increased bulkiness of the alkoxide moiety (including magnesium cation and ligands), followed by a resu...

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Detalles Bibliográficos
Autores principales: Song, Bo Reum, Ha, Min Woo, Kim, Donghwan, Park, Chanin, Lee, Keun Woo, Paek, Seung-Mann
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943632/
https://www.ncbi.nlm.nih.gov/pubmed/31888158
http://dx.doi.org/10.3390/molecules24244597
Descripción
Sumario:Employing iPrMgCl as an advanced base instead of lithium hexamethyldisilazane (LHMDS) resulted in dramatic improvements in aza-Claisen rearrangement. This advance is considered responsible for the increased bulkiness of the alkoxide moiety (including magnesium cation and ligands), followed by a resultant conformational change of the transition state. To support this hypothesis, various substrates of aza-Claisen rearrangement were prepared and screened. In addition, a molecular dynamic simulation study was performed to investigate and compare the structural stability of reaction intermediates.

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