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Issue 10, 2016

Enantioselective β-alkylation of pyrroles with the formation of an all-carbon quaternary stereocenter

Author affiliations

Abstract

A substitutionally and configurationally inert octahedral chiral-at-metal iridium complex is reported to be an efficient catalyst for the enantioselective Friedel–Crafts alkylation of 2,5-disubstituted pyrroles at the β-position using nitroacrylates as electrophiles. Catalysis is mediated through the ligand sphere of the bis-cyclometalated iridium complex by forming hydrogen bonds and van-der-Waals interactions with the substrates, providing β-alkylated pyrroles regioselectively in 75–98% yield and with 86–99% enantiomeric excess (19 examples). The products are versatile chiral building blocks as demonstrated by the reduction of the nitro group with complete retention of the chiral information.

Graphical abstract: Enantioselective β-alkylation of pyrroles with the formation of an all-carbon quaternary stereocenter

Supplementary files

Article information


Submitted
16 Jun 2016
Accepted
17 Aug 2016
First published
18 Aug 2016

Org. Chem. Front., 2016,3, 1319-1325
Article type
Research Article

Enantioselective β-alkylation of pyrroles with the formation of an all-carbon quaternary stereocenter

Q. Ma, L. Gong and E. Meggers, Org. Chem. Front., 2016, 3, 1319 DOI: 10.1039/C6QO00273K

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