STEREOSELECTIVE SYNTHESIS OF 2,3-DISUBSTITUTED GLUTAMIC-ACID DERIVATIVES BY CONJUGATE ADDITION TO 3,4-DIDEHYDROPYROGLUTAMATES

Authors
GUILLENA G MANCHENO B NAJERA C EZQUERRA J PEDREGAL C
Citation
G. Guillena et al., STEREOSELECTIVE SYNTHESIS OF 2,3-DISUBSTITUTED GLUTAMIC-ACID DERIVATIVES BY CONJUGATE ADDITION TO 3,4-DIDEHYDROPYROGLUTAMATES, Tetrahedron, 54(32), 1998, pp. 9447-9456
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
32
Year of publication
1998
Pages
9447 - 9456
Database
ISI
SICI code
0040-4020(1998)54:32<9447:SSO2GD>2.0.ZU;2-1
Abstract
The Michael addition of lithium or magnesium organocuprates and sodium dimethyl malonate to 2-alkylated 3,4-didehydropyroglutamates 7, prepa red 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 pyrogluta mates 9. Final hydrolysis of 9eb gives syn-2,3-disubstituted glutamic acid 10. (C) 1998 Elsevier Science Ltd. All rights reserved.