Asymmetric NHC-Catalyzed Redox α‑Amination of α‑Aroyloxyaldehydes

Asymmetric NHC-Catalyzed Redox α‑Amination of α‑Aroyloxyaldehydes

Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amin...

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Veröffentlicht in:Organic letters 2013-12, Vol.15 (23), p.6058-6061
Hauptverfasser: Taylor, James E, Daniels, David S. B, Smith, Andrew D
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Amination
Catalysis
Combinatorial Chemistry Techniques
Heterocyclic Compounds - chemistry
Hydrazines - chemistry
Iodides - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Oxidation-Reduction
Samarium - chemistry
Stereoisomerism
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Zusammenfassung:Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N–N bond cleavage.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402955f