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Volumn 45, Issue 21, 2004, Pages 4117-4121

Rh(I)-catalyzed ring-closing reaction of allenynes: Selective construction of cycloheptene, bicyclo[5.3.0]decadienone, and bicyclo[5.2.0]nonene frameworks

Author keywords

Allenyne; Bicyclo 5.2.0 nonane; Bicyclo 5.3.0 decane; Cycloisomerization; Electrocyclic reaction; Pauson Khand reaction

Indexed keywords

ALLENE DERIVATIVE; CYCLOHEPTENE; RHENIUM;

EID: 2342636512     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.160     Document Type: Article
Times cited : (61)

References (34)
  • 1
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    • For attempts at constructing the bicyclo[5.3.0]decenone skeleton via the intramolecular PKR of enynes, see:
    • For attempts at constructing the bicyclo[5.3.0]decenone skeleton via the intramolecular PKR of enynes, see: Wender P.A., McDonald F.E. Tetrahedron Lett. 31:1990;3691-3694
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3691-3694
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  • 3
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    • For construction of seven- and larger-membered rings via PKR of enynes with an aromatic ring as a template, see:
    • For construction of seven- and larger-membered rings via PKR of enynes with an aromatic ring as a template, see: Pérez-Serrano L., Casarrubios L., Domínguez G., Pérez-Castells J. Chem. Commun. 2001;2602-2603
    • (2001) Chem. Commun. , pp. 2602-2603
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  • 10
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    • 2-catalyzed PKR of allenynes, which involves four successful examples of the formation of the bicyclo[5.3.0]decadienone skeleton:
    • 2-catalyzed PKR of allenynes, which involves four successful examples of the formation of the bicyclo[5.3.0]decadienone skeleton: Brummond K.M., Chen H., Fisher K.D., Kerekes A.D., Rickards B., Sill P.C., Geib S.J. Org. Lett. 4:2002;1931-1934
    • (2002) Org. Lett. , vol.4 , pp. 1931-1934
    • Brummond, K.M.1    Chen, H.2    Fisher, K.D.3    Kerekes, A.D.4    Rickards, B.5    Sill, P.C.6    Geib, S.J.7
  • 12
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    • For other examples of the formation of the bicyclo[5.3.0]decane skeleton via transition metal-catalyzed PKR of allenynes, see:
    • For other examples of the formation of the bicyclo[5.3.0]decane skeleton via transition metal-catalyzed PKR of allenynes, see: Shibata T., Koga Y., Narasaka K. Bull. Chem. Soc. Jpn. 68:1995;911-919
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    • note
    • 2, 0°C
  • 15
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    • note
    • The bicyclo[4.3.0]nonenone derivative could never be detected in the reaction mixture
  • 20
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    • For reviews on cycloisomerization of enynes, see:
    • For reviews on cycloisomerization of enynes, see: Trost B.M. Acc. Chem. Res. 23:1990;34-42
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  • 22
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    • For Rh(I)-catalyzed enyne cycloisomerization, see:
    • For Rh(I)-catalyzed enyne cycloisomerization, see: Cao P., Wang B., Zhang X. J. Am. Chem. Soc. 122:2000;6490-6491
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  • 23
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    • For Rh(I)-catalyzed allenene cycloisomerization, see:
    • For Rh(I)-catalyzed allenene cycloisomerization, see: Makino T., Itoh K. Tetrahedron Lett. 44:2003;6335-6338
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    • 2-catalyzed construction of six-membered triene derivatives:
    • 2-catalyzed construction of six-membered triene derivatives: Brummond K.M., Chen H., Sill P., You L. J. Am. Chem. Soc. 124:2002;15186-15187
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  • 25
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    • 3-catalyzed reaction, developed by Shibata et al., has also been reported.
    • 3-catalyzed reaction, developed by Shibata et al., has also been reported. Shibata T., Takesue Y., Kadowaki S., Takagi K. Synlett. 2003;268-270
    • (2003) Synlett , pp. 268-270
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    • For other examples of transition metal-catalyzed allenyne cycloisomerizations, see:
    • For other examples of transition metal-catalyzed allenyne cycloisomerizations, see: Pagenkopf B.L., Belanger D.B., O'Mahony D.J.R., Livinghouse T. Synthesis. 2000;1009-1019
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    • note
    • 2 was shown to be fruitless in the transformation of 3d into 5d
  • 29
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    • Formation of fused cyclobutenes from allenynes has been reported. For transition metal-mediated cycloadditions, see:
    • Formation of fused cyclobutenes from allenynes has been reported. For transition metal-mediated cycloadditions, see: Shen Q., Hammond G.B. J. Am. Chem. Soc. 124:2002;6534-6535
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  • 31
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    • Formation of the bicyclo[5.2.0]nonene skeleton via thermolysis of 2-azetidinone-tethered enallenes has been reported:
    • Formation of the bicyclo[5.2.0]nonene skeleton via thermolysis of 2-azetidinone-tethered enallenes has been reported: Alcaide B., Almendros P., Aragoncillo C. Org. Lett. 5:2003;3795-3798
    • (2003) Org. Lett. , vol.5 , pp. 3795-3798
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 32
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    • note
    • 2 for 9 h provided 6e in 60% yield, along with recovered 5e (11%), whereas only 42% yield of 6e and 10% of the recovered 5e were obtained in the absence of Rh(I) catalyst for 9 h
  • 33
    • 2342458382 scopus 로고    scopus 로고
    • note
    • Refluxing 3f in xylene resulted in decomposition
  • 34
    • 2342636456 scopus 로고    scopus 로고
    • note
    • Allenyne having TMS group at the alkyne terminus afforded the corresponding bicyclo[5.2.0]nonene derivative in 34% yield


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.