Functionalisation of esters via 1,3-chelation using NaO t Bu: Mechanistic investigations and synthetic applications
- Authors
- Yang, H.S.[Yang, H.S.]; Macha, L.[Macha, L.]; Ha, H.-J.[Ha, H.-J.]; Yang, J.W.[Yang, J.W.]
- Issue Date
- Jan-2021
- Publisher
- Royal Society of Chemistry
- Citation
- Organic Chemistry Frontiers, v.8, no.1, pp.53 - 60
- Indexed
- SCIE
SCOPUS
- Journal Title
- Organic Chemistry Frontiers
- Volume
- 8
- Number
- 1
- Start Page
- 53
- End Page
- 60
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/92349
- DOI
- 10.1039/d0qo01135e
- ISSN
- 2052-4110
- Abstract
- 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 α-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. © 2021 the Partner Organisations.
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Collections - Graduate School > Energy Science > 1. Journal Articles
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