Enantioselective β-alkylation of pyrroles with the formation of an all-carbon quaternary stereocenter
Literature Information
Publication Date
2016-08-18
DOI
10.1039/C6QO00273K
Impact Factor
5.281
Authors
Qiao Ma, Lei Gong
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Molecular Formula:
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