Issue 40, 2015

Reversal of enantioselective Friedel–Crafts C3-alkylation of pyrrole by slightly tuning the amide units of N,N′-dioxide ligands

Abstract

Chiral Ni(II)-complexes of N,N′-dioxides show high catalytic activity and enantioselectivity in catalysing the asymmetric Friedel–Crafts C3-alkylation of 2,5-dimethyl pyrrole to β,γ-unsaturated α-ketoesters. A dramatic reversal of enantioselectivity is realized with ligands derived from the same type of chiral source of L-ramipril, by slightly tuning the amide units.

Graphical abstract: Reversal of enantioselective Friedel–Crafts C3-alkylation of pyrrole by slightly tuning the amide units of N,N′-dioxide ligands

Supplementary files

Article information

Article type
Communication
Submitted
17 Dec 2014
Accepted
05 Feb 2015
First published
18 Feb 2015

Chem. Commun., 2015,51, 8432-8435

Reversal of enantioselective Friedel–Crafts C3-alkylation of pyrrole by slightly tuning the amide units of N,N′-dioxide ligands

Y. Zhang, N. Yang, X. Liu, J. Guo, X. Zhang, L. Lin, C. Hu and X. Feng, Chem. Commun., 2015, 51, 8432 DOI: 10.1039/C4CC10055G

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