@article{3ffc258587ac4e6bad9c2999234e678c,
title = "Stereoselective synthesis of all individual isomers of β-methyl-2′,6′-dimethylphenylalanine",
abstract = "Asymmetric synthesis of all four isomers of β-methyl-2′,6′-dimethylphenylalanine was accomplished with complete stereoselectivities and high yields by using the Evans-like auxiliary 4-phenyl-oxazolidinone as a chiral auxiliary and as a chiral resolution reagent.",
keywords = "Asymmetric synthesis, Unusual amino acids, β-Methyl-2′,6′-dimethylphenylalanine",
author = "Li Xiang and Huiwei Wu and Hruby, {Victor J.}",
note = "Funding Information: The bromides 8a-Sd were then subjected to SN2 azide displacement reaction by using tetramethylguanidium azide 3b,4 in acetonitrile. The chiral auxiliary was removed and recycled by LiOH hydrolysis in the presence of hydrogen peroxide. The resulting azide acids 10a-10d were subjected to hydrogenation (10% Pd-C) at 34-38 psi for 24-48 hrs to yield the crude amino acids lla-lld which were purified by ion-exchange chromatography on Amberlite IR-120 plus exchange resin. No racemization was observed in all cases examined in this study. In summary, the first asymmetric synthesis of all four isomer of ~-methyl-2',6'-dimethylphenylalanine has been achieved using this strategy. The application of this method to the synthesis of other analogs of unusual amino acids is currently under investigation in our laboratory and has shown preliminary success. Two of the four isomers already are being used in peptide molecular design and have provided some interesting preliminary results. This work has been supported by U. S. Public Service Grants CA 57723 and DK 17420, and NIDA Grants DA 06284 and DA 04248. We would like to thank Mr. Guigen Li for his help during this research.",
year = "1995",
month = jan,
doi = "10.1016/0957-4166(94)00357-H",
language = "English (US)",
volume = "6",
pages = "83--86",
journal = "Tetrahedron: Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Ltd",
number = "1",
}