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Volumn 10, Issue 20, 2008, Pages 4441-4444

Rearrangement of spirocyclic oxindoles with lithium amide bases

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; AMIDE; INDOLE DERIVATIVE; LITHIUM; OXINDOLE; SPIRO COMPOUND;

EID: 58149144478     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8016885     Document Type: Article
Times cited : (26)

References (28)
  • 13
    • 61349095280 scopus 로고    scopus 로고
    • 3H was shown to lead exclusively to the expoxidation syn relative to the C=O group, likely as a result of the amide functional group directing effect: Rousseau, G.; Robert, F.; Landais, Y. unpublished results.
    • 3H was shown to lead exclusively to the expoxidation syn relative to the C=O group, likely as a result of the amide functional group directing effect: Rousseau, G.; Robert, F.; Landais, Y. unpublished results.
  • 14
    • 34547172487 scopus 로고    scopus 로고
    • Selectivity for Synthesis
    • Elsevier Science: Oxford
    • Clayden, J. Organolithiums: Selectivity for Synthesis. Tetrahedon Organic Chemistry Series; Elsevier Science: Oxford, 2002; Vol. 23.
    • (2002) Tetrahedon Organic Chemistry Series , vol.23
    • Clayden, J.O.1
  • 21
    • 0020246368 scopus 로고    scopus 로고
    • The relative configuration of alcohol 7a results from an ul-addition, involving the Si-face of the enolate and the Re-face of the aldehyde, through a transition state in which the aldehyde carbonyl group is likely coordinated to the lithium cation. Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654-660.
    • The relative configuration of alcohol 7a results from an ul-addition, involving the Si-face of the enolate and the Re-face of the aldehyde, through a transition state in which the aldehyde carbonyl group is likely coordinated to the lithium cation. Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654-660.
  • 24
    • 61349141165 scopus 로고    scopus 로고
    • Involvement of anionic species such as aryllithium or acyllithium intermediates formed through C1-C3 or C1-C2 bond breaking should not be ruled out. These would then recombine to afford iii.
    • Involvement of anionic species such as aryllithium or acyllithium intermediates formed through C1-C3 or C1-C2 bond breaking should not be ruled out. These would then recombine to afford iii.
  • 28
    • 61349124792 scopus 로고    scopus 로고
    • The relative configuration of 14 was determined through X-ray diffraction analysis (see Supporting Information).
    • The relative configuration of 14 was determined through X-ray diffraction analysis (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.