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Stereoselective synthesis of 2,3-disubstituted glutamic acid derivatives by conjugate addition to 3,4-didehydropyroglutamates

✍ Scribed by Gabriela Guillena; Balbino Mancheño; Carmen Nájera; Jesús Ezquerra; Concepción Pedregal

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 635 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00573-0

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✦ Synopsis

The Michael addition of lithium or magnesium organocuprates and sodium dimethyl malonate to 2-alkylated 3,4-didehydropymglutamates 7, prepared from the corresponding 4-substituted sulfoxides pyroglutamates or from benzophenone imine of glycine ethyl ester or nittile, takes place in a stereoselective manner affording cis-2,3-disubstituted pyroglutamates 9. Final hydrolysis of 9eb gives syn-2,3-disubstituted glutamic acid 10.

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