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Volumn , Issue 45, 2007, Pages 4788-4790

Direct organocatalytic synthesis of enantiopure succinimides from β-lactam aldehydes through ring expansion promoted by azolium salt precatalysts

Author keywords

[No Author keywords available]

Indexed keywords

4 OXOAZETIDINE 2 CARBALDEHYDE; ALDEHYDE DERIVATIVE; BASE; BETA LACTAM DERIVATIVE; SODIUM CHLORIDE; SUCCINIMIDE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36148990212     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b711473g     Document Type: Article
Times cited : (54)

References (23)
  • 2
    • 36148991120 scopus 로고    scopus 로고
    • WO2004110437 Organon Ireland Ltd, Ire.), PCT Int. Appl.
    • J. Tonnaer and D. M. Alphons (Organon Ireland Ltd, Ire.), PCT Int. Appl., 2004, WO2004110437
    • (2004)
    • Tonnaer, J.1    Alphons, D.M.2
  • 18
    • 36148961258 scopus 로고    scopus 로고
    • 1H NMR spectra in presence of a chiral shift reagent of europium(iii), except for phthalimidoyl succinimide 4c which was obtained in 50% ee. It is well known that the structurally related thalidomide may suffer racemization even at physiological conditions. See:
    • No succinimides were produced in the absence of the catalyst or in the presence of azolium salt or base on their own
  • 22
    • 0028220747 scopus 로고
    • It was observed that the organocatalyzed reaction of β-lactam aldehyde 1f yielded as main product succinimide 4f, together with maleimide 5 (Scheme 1). The formation of compound 5 involves methanol elimination under the reaction conditions to relieve the strain Optically pure trans-4-oxoazetidine-2- carbaldehyde (+)-epim- 1a was prepared as reported, see:
    • B. Knoche G. Blaschke J. Chromatogr., A 1994 666 235
    • (1994) J. Chromatogr., a , vol.666 , pp. 235
    • Knoche, B.1    Blaschke, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.