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Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids

✍ Scribed by Martin Smrcina; Pavel Majer; Eva Majerová; Tatiana A. Guerassina; Michael A. Eissenstat

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
459 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

A lacile slereoselcctive melhod Ior the synthesis of y-substituted, y-mnino acids from of amino acids was developed. The key step of the procedurc is complete reduction of Ihe keto functionality of ot-~unino acyl Meldruln's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields Ihe correslxmding y-amino acid after ~sic hydrolysis. The over',dl yield of the procedure ranges ti'om 40 to 65~7,.

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