Efficient enzymatic approach to (S)-1-aryl-allylamines (CROSBI ID 174452)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Knežević, Anamarija ; Landek, Goran ; Dokli, Irena ; Vinković, Vladimir
engleski
Efficient enzymatic approach to (S)-1-aryl-allylamines
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.
aryl-allylamines ; Candida antarctica B ; Overman rearrangement ; enantioselectivity
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Podaci o izdanju
22 (9)
2011.
936-941
objavljeno
0957-4166
1362-511X
10.1016/j.tetasy.2011.06.004