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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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
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author Song, Bo Reum
Ha, Min Woo
Kim, Donghwan
Park, Chanin
Lee, Keun Woo
Paek, Seung-Mann
author_facet Song, Bo Reum
Ha, Min Woo
Kim, Donghwan
Park, Chanin
Lee, Keun Woo
Paek, Seung-Mann
author_sort Song, Bo Reum
collection PubMed
description 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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spelling pubmed-69436322020-01-10 Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement Song, Bo Reum Ha, Min Woo Kim, Donghwan Park, Chanin Lee, Keun Woo Paek, Seung-Mann Molecules Article 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. MDPI 2019-12-16 /pmc/articles/PMC6943632/ /pubmed/31888158 http://dx.doi.org/10.3390/molecules24244597 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Song, Bo Reum
Ha, Min Woo
Kim, Donghwan
Park, Chanin
Lee, Keun Woo
Paek, Seung-Mann
Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title_full Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title_fullStr Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title_full_unstemmed Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title_short Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
title_sort investigation of grignard reagent as an advanced base for aza-claisen rearrangement
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943632/
https://www.ncbi.nlm.nih.gov/pubmed/31888158
http://dx.doi.org/10.3390/molecules24244597
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