Catalytic Enantioselective Synthesis of N-C Axially Chiral N -(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N -Allylation

Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic heterocycle skeletons. On the other hand, although...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-11, Vol.27 (22), p.7819
Main Authors: Fukasawa, Sota, Toyoda, Tatsuya, Kasahara, Ryohei, Nakamura, Chisato, Kikuchi, Yuuki, Hori, Akiko, Richards, Gary J, Kitagawa, Osamu
Format: Article
Language:English
Subjects:
Acetic acid
Allyl compounds
Antibiotics
asymmetric catalyst
atropisomers
axial chirality
Catalysis
Catalysts
Chemical reactions
Enantiomers
Heterocyclic compounds
Ligands
N-allylation
Nitrogen
Palladium
Palladium - chemistry
Single crystals
Stereochemistry
Stereoisomerism
Structural analysis
Sulfanilamide
Sulfonamides
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Summary:Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic heterocycle skeletons. On the other hand, although N-C axially chiral sulfonamide derivatives are known, their catalytic enantioselective synthesis is relatively underexplored. We found that the reaction (Tsuji-Trost allylation) of allyl acetate with secondary sulfonamides bearing a 2-arylethynyl-6-methylphenyl group on the nitrogen atom proceeds with good enantioselectivity (up to 92% ee) in the presence of ( , )-Trost ligand-(allyl-PdCl) catalyst, affording rotationally stable N-C axially chiral -allylated sulfonamides. Furthermore, the absolute stereochemistry of the major enantiomer was determined by X-ray single crystal structural analysis and the origin of the enantioselectivity was considered.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27227819