Convenient, asymmetric synthesis of enantiomerically pure 2',6'- dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine

Xuejun Tang, Vadim A. Soloshonok, Victor J. Hruby

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Abstract

Asymmetric synthesis of (S)-2',6'-dimethyltyrosine (DMT) via reactions of 4'-benzyloxy-2',6'-dimethylbenzyl bromide with Ni(II)-complexes of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]- benzophenone was developed. Inexpensive and readily available reagents and solvents involved, including recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical yields, make this method synthetically attractive for preparing the target amino acids on a multi-gram scale. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)2917-2925
Number of pages9
JournalTetrahedron Asymmetry
Volume11
Issue number14
DOIs
StatePublished - Jul 28 2000

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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