Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 1, Pages 53-60Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01135e
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Funding
- NRF Programs [2019R1A2C1003276, 2019R1A4A2001440]
- NRF Nano.Material Technology Development Program [2012M3A7B4049645]
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The study confirmed that 1,3-chelation and the formation of a tetrahedral intermediate play crucial roles in the unusual nucleophilic behavior of a metal t-butoxide in a transesterification reaction. Mechanistic investigations using NMR and real-time IR spectroscopies demonstrated the possibility of achieving value-added reactions based on the understanding of the t-butoxide anion action.
For the first time, both 1,3-chelation and the formation of a tetrahedral intermediate were confirmed as the key factors for the unusual nucleophilic behavior of a metal t-butoxide in a transesterification reaction. NMR and real-time IR spectroscopies and deuterium-labeling experiments were used for the mechanistic investigation. Based on a pivotal point in the mechanistic understanding of the action of t-butoxide anion, several uncovering reactions such as direct access to value-added chiral alpha-amino acid t-butyl ester with almost complete retention of optical purity via elaborative transesterification, non-hydrolytic deesterification of esters, and selective bond cleavage of 3-benzoyloxazolidin-2-ones, were successfully achieved.
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