Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangementopen access
- Song, Bo Reum; Ha, Min Woo; Kim, Donghwan; Park, Chanin; Lee, Keun Woo; Paek, Seung-Mann
- Issue Date
- aza-Claisen rearrangement; Grignard reagent; ring expansion; base; molecular dynamics
- MOLECULES, v.24, no.24
- Journal Title
- 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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- 약학대학 > 약학과 > Journal Articles
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