Issue 1, 2021

Functionalisation of esters via 1,3-chelation using NaOtBu: mechanistic investigations and synthetic applications

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.

Graphical abstract: Functionalisation of esters via 1,3-chelation using NaOtBu: mechanistic investigations and synthetic applications

Supplementary files

Article information

Article type
Research Article
Submitted
17 Sep 2020
Accepted
02 Nov 2020
First published
03 Nov 2020

Org. Chem. Front., 2021,8, 53-60

Functionalisation of esters via 1,3-chelation using NaOtBu: mechanistic investigations and synthetic applications

H. S. Yang, L. Macha, H. Ha and J. W. Yang, Org. Chem. Front., 2021, 8, 53 DOI: 10.1039/D0QO01135E

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