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

Add time:08/08/2019    Source:sciencedirect.com

The Michael addition of lithium or magnesium organocuprates and sodium dimethyl malonate to 2-alkylated 3,4-didehydropyroglutamates 7, prepared from the corresponding 4-substituted sulfoxides pyroglutamates or from benzophenone imine of glycine ethyl ester or nitrile, 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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