Issue 41, 2023
From the journal:

Organic & Biomolecular Chemistry

Borane catalyzed transesterification of tert-butyl esters using α-aryl α-diazoesters†

Maying Yan, ORCID logo ‡a   Lei Xiao, ORCID logo ‡a   Jiangkun Xiong, ORCID logo a   Lvnan Jin, ORCID logo a   Douglas W. Stephan ORCID logo *ab  and  Jing Guo ORCID logo *a  

* Corresponding authors

a Institute of Drug Discovery Technology, Ningbo University, Zhejiang, China
E-mail: guojing@nbu.edu.cn

b Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada
E-mail: dstephan@chem.utoronto.ca

Abstract

The B(C6F5)3-catalyzed transesterification of a series of 3-alkenyl-oxindoles and other unsaturated tert-butyl esters with aryl-diazo esters is reported. This protocol is facile and generally high yielding proceeding under mild conditions and is remarkably chemoselective leaving the C[double bond, length as m-dash]C bonds intact.

Graphical abstract: Borane catalyzed transesterification of tert-butyl esters using α-aryl α-diazoesters

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Article information

DOI
https://doi.org/10.1039/D3OB01548C
Article type
Communication
Submitted
25 Sep 2023
Accepted
03 Oct 2023
First published
04 Oct 2023

Org. Biomol. Chem., 2023,21, 8279-8283

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Borane catalyzed transesterification of tert-butyl esters using α-aryl α-diazoesters

M. Yan, L. Xiao, J. Xiong, L. Jin, D. W. Stephan and J. Guo, Org. Biomol. Chem., 2023, 21, 8279 DOI: 10.1039/D3OB01548C

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