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Synthesis of γ-hydroxy-α-amino acids by directed hydroxylation via a dihydro-1,3-oxazine intermediate.

✍ Scribed by Alberto Avenoza; Carlos Cativiela; Jesús M. Peregrina

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 531 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89617-4

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✦ Synopsis

The amide group of y&unsaturated amino acids can be used for the preparation of yhydroxya-amino acids. Product 2, which is easily obtained by hydrolysis of the spiro-oxazoloneadduct formed in the Diels-Alder reaction between (Z)-2-phenyl-4-benzylidene-5(4H)-oxaxolone 1 and 1,3butadiene. was converted into the corresponding iodo-1,3-oxazine 3 with Iddioxane. Further deiodination and hydrolysis of this product allows the obtention of the free y-hydroxy-a-amino acid 8.

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