Synthesis of 2,6-Dimethyltyrosine-Like Amino Acids through Pinacolinamide-Enabled C–H Dimethylation of 4-Dibenzylamino Phenylalanine - Institut Parisien de Chimie Moléculaire Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2022

Synthesis of 2,6-Dimethyltyrosine-Like Amino Acids through Pinacolinamide-Enabled C–H Dimethylation of 4-Dibenzylamino Phenylalanine

Résumé

The synthesis of a small library of NH-Boc- or NH-Fmoc-protected l-phenylalanines carrying methyl groups at positions 2 and 6 and diverse functionalities at position 4 has been achieved. The approach, which took advantage of a Pd-catalyzed directed C–H dimethylation of picolinamide derivatives, allowed the electronic and steric properties of the resulting amino acid derivatives to be altered by appending a variety of electron-withdrawing, electron-donating, or bulky groups.
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Dates et versions

hal-03566662 , version 1 (11-02-2022)

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Davide Illuminati, Anna Fantinati, Tiziano de Ventura, Daniela Perrone, Chiara Sturaro, et al.. Synthesis of 2,6-Dimethyltyrosine-Like Amino Acids through Pinacolinamide-Enabled C–H Dimethylation of 4-Dibenzylamino Phenylalanine. Journal of Organic Chemistry, 2022, pp.acs.joc.1c02527. ⟨10.1021/acs.joc.1c02527⟩. ⟨hal-03566662⟩
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