TY - JOUR
T1 - Convenient, asymmetric synthesis of enantiomerically pure 2',6'- dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine
AU - Tang, Xuejun
AU - Soloshonok, Vadim A.
AU - Hruby, Victor J.
N1 - Funding Information:
This work was supported by grants from the US Public Health Service and The National Institute of Drug Abuse DA 06284, DA 04248 and DK 17420. The views expressed are those of the authors and not necessarily of the USPHS.
PY - 2000/7/28
Y1 - 2000/7/28
N2 - 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.
AB - 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.
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U2 - 10.1016/S0957-4166(00)00250-0
DO - 10.1016/S0957-4166(00)00250-0
M3 - Article
AN - SCOPUS:0034725677
SN - 0957-4166
VL - 11
SP - 2917
EP - 2925
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 14
ER -