Tetrahedron: Asymmetry

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

X Tang, VA Soloshonok, VJ Hruby

Index: Tang, Xuejun; Soloshonok, Vadim A.; Hruby, Victor J. Tetrahedron Asymmetry, 2000 , vol. 11, # 14 p. 2917 - 2925

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Citation Number: 61

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 ...