Issue 8, 2019

Stereoselective C-terminal peptide elongation from Chan–Lam–Evans reaction generated isopropenyl esters

Abstract

C-Terminal dipeptide isopropenyl esters were synthesised by a Cu(II)-mediated Chan–Lam–Evans enol esterification of peptide carboxylic acids and isoprenyl boroxine. These shelf stable peptide esters could be coupled stereoselectively with a variety of amino acid and dipeptide nucleophiles in high yield and purity in the presence of pyrazole/DBU as the catalyst.

Graphical abstract: Stereoselective C-terminal peptide elongation from Chan–Lam–Evans reaction generated isopropenyl esters

Supplementary files

Article information

Article type
Communication
Submitted
28 Aug 2018
Accepted
19 Sep 2018
First published
04 Feb 2019
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2019,17, 2103-2106

Stereoselective C-terminal peptide elongation from Chan–Lam–Evans reaction generated isopropenyl esters

L. Steemers and J. H. van Maarseveen, Org. Biomol. Chem., 2019, 17, 2103 DOI: 10.1039/C8OB02102C

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