Issue 4, 2015

1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures

Abstract

A diversity of new functionalized acyclic chiral pyrroloamide compounds were synthesized by a simple and robust process involving the creation of a C–C bond between unprotected pyrroles and acyclic chiral acrylamides using Lewis acids. This alkylation reaction using Michael acceptors has been optimized, allowing us to obtain channel selective access to monoalkylated or dialkylated pyrroles, in good yields. Di- and tripeptide deriving acrylamides have also been used as the reaction partner.

Graphical abstract: 1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures

Supplementary files

Article information

Article type
Paper
Submitted
10 Sep 2014
Accepted
10 Nov 2014
First published
10 Nov 2014

Org. Biomol. Chem., 2015,13, 1082-1090

1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures

A. Gratais, X. Pannecoucke and S. Bouzbouz, Org. Biomol. Chem., 2015, 13, 1082 DOI: 10.1039/C4OB01920B

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