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A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids

✍ Scribed by Alessandra Maria Nocioni; Carmela Papa; Claudia Tomasini

Book ID
104262550
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
215 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The diastereoselective synthesis of syn-a-alkyl a-hydroxy 13-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti a-alky113-benzoylamino acid methyl esters with iodine. The intermediate a-iodo derivatives spontaneously afforded c/s-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1.

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