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

Research output: Contribution to journalArticle

74 Citations (Scopus)

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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Schiff Bases
alkylation
Alkylation
glycine
Bromides
Glycine
imines
reagents
amino acids
Amino acids
bromides
Amino Acids
synthesis
benzophenone
2',6'-dimethyltyrosine

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Convenient, asymmetric synthesis of enantiomerically pure 2',6'- dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine. / Tang, Xuejun; Soloshonok, Vadim A.; Hruby, Victor J.

In: Tetrahedron Asymmetry, Vol. 11, No. 14, 28.07.2000, p. 2917-2925.

Research output: Contribution to journalArticle

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