Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide electrophiles

Amide cross-couplings that rely on C-N bond activation by transition metal catalysts have emerged as valuable synthetic tools. Despite numerous discoveries in this field, no catalytic asymmetric variants have been disclosed to date. Herein, we demonstrate the first such transformation, which is the...

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Published inChemical science (Cambridge) Vol. 15; no. 7; pp. 2593 - 2600
Main Authors Bulger, Ana S., Nasrallah, Daniel J., Meza, Arismel Tena, Garg, Neil K.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.02.2024
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Asymmetry
Catalysis
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Couplings
Enantiomers
Nickel
Physical Sciences
Science & Technology
Substrates
Transition metals
CROSS-COUPLING REACTIONS
ACTIVATION
C-O
KETONE SYNTHESIS
ARYL ESTERS
COMPLEXES
ALKENE CARBOACYLATION
ACYL-OXYGEN BONDS
CLEAVAGE
ACCESS
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Summary:Amide cross-couplings that rely on C-N bond activation by transition metal catalysts have emerged as valuable synthetic tools. Despite numerous discoveries in this field, no catalytic asymmetric variants have been disclosed to date. Herein, we demonstrate the first such transformation, which is the Mizoroki-Heck cyclization of amide substrates using asymmetric nickel catalysis. This proof-of-concept study provides an entryway to complex enantioenriched polycyclic scaffolds and advances the field of amide C-N bond activation chemistry. The first asymmetric amide cross-couplings that rely on C-N bond activation using transition metal catalysis are reported. The study establishes a new avenue in amide C-N bond activation chemistry.
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These authors contributed equally to this work.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc05797f