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Volumn 15, Issue 15, 2013, Pages 4002-4005

Synthesis of 3,3′-spirocyclic oxindoles via phosphine catalyzed [4 + 2] cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; OXINDOLE; PHOSPHINE; PHOSPHINE DERIVATIVE; SPIRO COMPOUND; TRIPHENYLPHOSPHINE;

EID: 84881254291     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401798w     Document Type: Article
Times cited : (114)

References (52)
  • 24
    • 84881222585 scopus 로고    scopus 로고
    • (Hoffmann-La Roche AG) PCT Int. Appl. WO2008/055812
    • Liu, J.-J.; Zhang, Z. (Hoffmann-La Roche AG) PCT Int. Appl. WO2008/055812, 2008.
    • (2008)
    • Liu, J.-J.1    Zhang, Z.2
  • 41
    • 64349119102 scopus 로고    scopus 로고
    • Substituted allenoates have been used also as two-atom components in 4 + 2 cyclizations
    • γ-Substituted allenoates have been used also as two-atom components in 4 + 2 cyclizations: Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991
    • (2009) Org. Lett. , vol.11 , pp. 991
    • Meng, X.1    Huang, Y.2    Zhao, H.3    Xie, P.4    Ma, J.5    Chen, R.6
  • 43
    • 84881234004 scopus 로고    scopus 로고
    • An alternative reaction pathway might involve the allylic phosphorus ylide II ′ as the reaction intermediate
    • An alternative reaction pathway might involve the allylic phosphorus ylide II ′ as the reaction intermediate.
  • 44
    • 84881243870 scopus 로고    scopus 로고
    • The six-membered ring might also be formed by a Diels-Alder type reaction between the olefin and a conjugated diene generated by isomerization of the allenoate. A Diels-Alder process is expected however to take place with retention of the geometry of the starting olefin. Moreover, we did not observe any cycloaddition product when heating a mixture of 3a and ethyl 5-phenyl-2,4-pentadienoate
    • The six-membered ring might also be formed by a Diels-Alder type reaction between the olefin and a conjugated diene generated by isomerization of the allenoate. A Diels-Alder process is expected however to take place with retention of the geometry of the starting olefin. Moreover, we did not observe any cycloaddition product when heating a mixture of 3a and ethyl 5-phenyl-2,4-pentadienoate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.