4.7 Article

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

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 5, 页码 2580-2589

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02527

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资金

  1. CNRS
  2. Sorbonne Universite
  3. Marie Sklodowska-Curie Innovative Training Network European Training Networks (ITN-ETN) C-H Activation for Industrial Renewal

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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 synthesized through a Pd-catalyzed directed C-H dimethylation. The electronic and steric properties of the resulting amino acid derivatives can be altered by appending a variety of electron-withdrawing, electron-donating, or bulky groups.
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 functionalitics 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 electronwithdrawing, electron-donating, or bulky groups.

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