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Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives

✍ Scribed by Christopher J. Easton; Craig A. Hutton; Peter D. Roselt; Edward R.T. Tiekink

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
1018 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

&s&z& Sideshain bmmiion of N-phthaloyl-Q-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous ace4one. affords the corresponding (2s3R)-b-hydroxy-a-amino acids, enantiospeci&ally and diastexxxelectively. The mlwtivity depend9 on the carboxy protecting group.

re+Butyl esters display gnzater stereoselectivity than the correqonding methyl esters, presumably BS a result of a stexic effect, while N-tert-butylamides react diastenospecifrall due to a combination of s&sic and electronic effects.

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