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

Org Biomol Chem

Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.

Published: February 2019

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.

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http://dx.doi.org/10.1039/c8ob02102cDOI Listing

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