Remote O, C-dianion chemistry of pyroglutamates: Reaction at C-4 with electrophiles

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4411-4412

  Dikshit, Dinesh K ^a   Maheshwari, Anjana ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; PYROGLUTAMIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; COLUMN CHROMATOGRAPHY; ELECTROCHEMISTRY; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT;

EID: 0033523034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00759-5     Document Type: Article

References (29)

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25. N-Arylmethylpyroglutamic acids were prepared according to Quitt, P., Hellerbach, J; & Vogler, K. Helv. Chim. Acta 1963, 46, 327 and N-methylpyroglulamic acid was prepared by the hydrolysis of the corresponding ester synthesized by the procedure of Cauliez, P.; Rigo, B.; Fasseur, D., Couturier, D. J. Heterocycl. Chem. 1991, 28, 1143.
26. N-Arylmethylpyroglutamic acids were prepared according to Quitt, P., Hellerbach, J; & Vogler, K. Helv. Chim. Acta 1963, 46, 327 and N-methylpyroglulamic acid was prepared by the hydrolysis of the corresponding ester synthesized by the procedure of Cauliez, P.; Rigo, B.; Fasseur, D., Couturier, D. J. Heterocycl. Chem. 1991, 28, 1143.
27. 2) for its comparison with a previously made sample. 3h was assigned 4-αa stereochemistry on the basis of N.O.E.
28. (b) Yields: 2a, 56; 2b, 52; 2c, 54; 3a, 58; 3b, 50; 3c, 50; 3e 54; 3f, 60; 3g, 48; 3h, 8%. Low yields of 4-methylated products have also been reported previously (Ezquerra, J; Pedregal, C; Rubio, A; Yruretagoyena, B; Escribano, A; Ferrando, F.S. Tetrahedron 1993, 49, 8665).
29. (c) The presence of the 4-cis products was not observed by the tlc of the crude reaction mixtures.