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Efficient enzymatic approach to (S)-1-aryl-allylamines


Knežević, Anamarija; Landek, Goran; Dokli, Irena; Vinković, Vladimir
Efficient enzymatic approach to (S)-1-aryl-allylamines // Tetrahedron: asymmetry, 22 (2011), 9; 936-941 doi:10.1016/j.tetasy.2011.06.004 (međunarodna recenzija, članak, znanstveni)


Naslov
Efficient enzymatic approach to (S)-1-aryl-allylamines

Autori
Knežević, Anamarija ; Landek, Goran ; Dokli, Irena ; Vinković, Vladimir

Izvornik
Tetrahedron: asymmetry (0957-4166) 22 (2011), 9; 936-941

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Aryl-allylamines ; Candida antarctica B ; Overman rearrangement ; enantioselectivity

Sažetak
A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%→99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3, 3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982904-2910 - Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja (Vladimir Vinković, )
098-0982933-2908 - Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost (Zdenko Hameršak, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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