Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives

Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives

The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral...

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Veröffentlicht in:Organic letters 2011-11, Vol.13 (21), p.5792-5795
Hauptverfasser: Nakanishi, Masafumi, Minard, Corinne, Retailleau, Pascal, Cariou, Kevin, Dodd, Robert H
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Amides - chemistry
Amination
Catalysis
Chemical Sciences
Copper - chemistry
Ligands
Molecular Structure
Organic chemistry
Stereoisomerism
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Zusammenfassung:The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202367d