A CONVENIENT ASYMMETRIC-SYNTHESIS OF THE UNNATURAL AMINO-ACID 2,6-DIMETHYL-L-TYROSINE

The title compound was prepared in high optical purity by a five-step synthesis from 3,5-dimethylphenol on a kilogram scale. The key steps were a modified palladium-catalyzed coupling of an aryl iodide with methyl 2-acetamidoacrylate and hydrogenation of the resulting sterically hindered dehydroamin...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 8; pp. 741 - 743
Main Authors DYGOS, JH, YONAN, EE, SCAROS, MG, GOODMONSON, OJ, GETMAN, DP, PERIANA, RA, BECK, GR
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
ORGANIC HALIDES
HYDROGENATION
DERIVATIVES
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Summary:The title compound was prepared in high optical purity by a five-step synthesis from 3,5-dimethylphenol on a kilogram scale. The key steps were a modified palladium-catalyzed coupling of an aryl iodide with methyl 2-acetamidoacrylate and hydrogenation of the resulting sterically hindered dehydroamino acid 4 using [Rh(1,5-COD)-(R,R-DIPAMP)]BF4 as catalyst.
ISSN:0039-7881
DOI:10.1055/s-1992-26212