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Volumn 8, Issue 3, 2006, Pages 459-462

Ring-opening/ring-closing metathesis (RORCM) reactions of 7-azanorbornene derivatives. An entry into perhydroindolines

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EID: 32644451000     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052741g     Document Type: Article
Times cited : (49)

References (59)
  • 1
    • 13244289910 scopus 로고    scopus 로고
    • For recent reviews see: (a) Astruc, D. New J. Chem. 2005, 29, 42.
    • (2005) New J. Chem. , vol.29 , pp. 42
    • Astruc, D.1
  • 40
    • 32644444449 scopus 로고    scopus 로고
    • note
    • When run in the absence of ethylene the RORCM reaction of 23 gave a mixture of product 27 and unidentified oligomer (we have occasionally observed minor amounts (<5%) of oligomer from the RORCM reactions run in the presence of ethylene). We have not isolated any of the divinyl pyrrolidine intermediate expected from a stepwise reaction when the reaction was run in the presence of ethylene. Others have also reported the importance of ethylene to inhibit oligomer formation in related reactions. For example, see ref 81.
  • 48
    • 0034727941 scopus 로고    scopus 로고
    • For synthetic work from other labs that targets perhydroindolines see: (a) Wipf, P.; Methot, J.-L. Org. Lett. 2000, 2, 4213.
    • (2000) Org. Lett. , vol.2 , pp. 4213
    • Wipf, P.1    Methot, J.-L.2
  • 52
    • 0000140103 scopus 로고    scopus 로고
    • While our plan had been to employ ester dienophiles as precursors to the desired substrates, the Diels-Alder cycloaddition reaction between N-Boc pyrrole and any number of ester dienenophiles (i.e., methyl acrylate, acrylaldehyde, ethyl propiolate, and methyl vinyl ketone) failed to give the corresponding 7-azanorbornenes in our hands. For a review on pyrrole Diels-Alder chemistry see: Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
    • (1996) Chem. Rev. , vol.96 , pp. 1179
    • Chen, Z.1    Trudell, M.L.2
  • 53
    • 32644452637 scopus 로고    scopus 로고
    • note
    • Perhydroindolines 25 and 27 also underwent efficient bromocyclization reactions.
  • 59
    • 32644448893 scopus 로고    scopus 로고
    • note
    • Interestingly, the C(1) acid from TBS ether 27 did not undergo the bromolactonization reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.