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Volumn 74, Issue 21, 2009, Pages 8410-8413

An efficient synthetic approach to polycyclic 2,5-dihydropyrroles from α-silyloxy ketones

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDES; CHEMICAL EQUATIONS; DIASTEREOMERS; DIHYDROPYRROLE; LEWIS ACID; SILYL ESTERS; STEP SEQUENCES; SYNTHETIC APPROACH;

EID: 70350719267     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901978y     Document Type: Article
Times cited : (20)

References (35)
  • 2
    • 70350740347 scopus 로고    scopus 로고
    • Macor, J. E., Ed.
    • (a) Macor, J. E., Ed. Annu. Rep. Med. Chem. 2008, 43.
    • (2008) Annu. Rep. Med. Chem. , vol.43
  • 3
    • 70350730852 scopus 로고    scopus 로고
    • Macor, J. E., Ed.
    • (b) Macor, J. E., Ed. Annu. Rep. Med. Chem. 2007, 42.
    • (2007) Annu. Rep. Med. Chem. , vol.42
  • 4
    • 84944034609 scopus 로고
    • Application as Pharmaceuticals
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York
    • (c) Landquist, J. K. Application as Pharmaceuticals. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol.1, pp 143-183.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.1 , pp. 143-183
    • Landquist, J.K.1
  • 14
    • 0004101860 scopus 로고
    • For reviews on the generation and reactivity of azomethine ylides see: (a) Wiley: New York
    • For reviews on the generation and reactivity of azomethine ylides see: (a) Padwa, A. 1,3-dipolar cycloaddition chemistry;Wiley: New York, 1984.
    • (1984) 1,3-dipolar Cycloaddition Chemistry
    • Padwa, A.1
  • 15
    • 0000629986 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: London, UK
    • (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, UK, 1991; Vol.4, p 1069.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069
    • Padwa, A.1
  • 22
    • 0038141659 scopus 로고
    • For intramolecular reactions of ynoates with azomethine ylides generated from oxazolines see: (a)
    • For intramolecular reactions of ynoates with azomethine ylides generated from oxazolines see: (a) Vedejs, E.; Dax, S. L. Tetrahedron Lett. 1989, 30, 2627.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2627
    • Vedejs, E.1    Dax, S.L.2
  • 30
    • 0031053010 scopus 로고    scopus 로고
    • In some cases, the silyl ester was contaminated with the N,O-bissilyl amino acid derivative. These mixtures were equally effective in the cycloaddition reactions
    • (b) Annunziata, R.; Ferrari, M.; Papeo, G.; Resmini, M.; Sisti, M. Synth. Commun. 1997, 27, 23. In some cases, the silyl ester was contaminated with the N,O-bissilyl amino acid derivative. These mixtures were equally effective in the cycloaddition reactions.
    • (1997) Synth. Commun. , vol.27 , pp. 23
    • Annunziata, R.1    Ferrari, M.2    Papeo, G.3    Resmini, M.4    Sisti, M.5
  • 34
    • 70350721005 scopus 로고    scopus 로고
    • The relative configurations of compounds 6, 9, 15, 20, and 25 were determined through NOE studies. The relative stereochemistry depicted for the remaining compounds was based on analogy
    • The relative configurations of compounds 6, 9, 15, 20, and 25 were determined through NOE studies. The relative stereochemistry depicted for the remaining compounds was based on analogy.


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