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Volumn 126, Issue 35, 2004, Pages 11058-11066

Catalytic intermolecular Pauson-Khand-type reaction: Strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction

Author keywords

[No Author keywords available]

Indexed keywords

INTERMOLECULAR REACTIONS; PAUSON-KHAND-TYPE REACTIONS (PKR);

EID: 4444362831     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047484+     Document Type: Article
Times cited : (55)

References (158)
  • 9
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    • note
    • Although the term "Pauson-Khand reaction" applies only to Co-mediated process, we refer to any closely related metal-mediated or -catalyzed [2 + 2+1] cycloannulation process of alkyne, alkene, and carbon monoxide (or its equivalent such as isocyanide) as "Pauson-Khand-type reaction" (PKR) in this paper.
  • 66
    • 0001353739 scopus 로고
    • Ni-promoted cyclization of enynes with isocyanides was originally reported by Ito and Tamao: (a) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286-1288.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1286-1288
    • Tamao, K.1    Kobayashi, K.2    Ito, Y.3
  • 85
    • 0037123291 scopus 로고    scopus 로고
    • Rh-catalyzed intramolecular PKR of enynes using an aldehyde as a source of CO has been reported independently by two groups: (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002,124, 3806-3807.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3806-3807
    • Morimoto, T.1    Fuji, K.2    Tsutsumi, K.3    Kakiuchi, K.4
  • 91
    • 0000458209 scopus 로고
    • For excellent reviews on directed chemical reactions, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 112
    • 0032567406 scopus 로고    scopus 로고
    • Though not PKR, Itoh and Yamamoto have found the beneficial effect of a coordinating atom in several catalytic cycloaddition reactions: (a) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610-9611.
    • (1998) J. Org. Chem. , vol.63 , pp. 9610-9611
    • Yamamoto, Y.1    Kitahara, H.2    Ogawa, R.3    Itoh, K.4
  • 127
    • 0000087962 scopus 로고
    • For the use of removable directing groups for metal-catalyzed and -mediated reactions, see: (a) Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917-6918.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6917-6918
    • Evans, D.A.1    Fu, G.C.2    Hoveyda, A.H.3
  • 130
  • 139
    • 4444381787 scopus 로고    scopus 로고
    • note
    • See Supporting Information for the synthetic scope (including the previous published materials) of the Ru-catalyzed intermolecular PKR.
  • 140
    • 4444255469 scopus 로고    scopus 로고
    • note
    • Under identical conditions, the reaction of dimethyl(2-pyridyl)(vinyl) silane (1) and phenylacetylene (4a) furnished 2-phenyl-2-cyclopentenone (5a) in 55% yield.
  • 149
    • 0000328103 scopus 로고
    • Selected examples for the isolation of late-metal metallacyclopentenes relevant to transition-metal-catalyzed reactions: (a) Wakatsuki, Y.; Aoki, K.; Yamazaki, H. J. Am. Chem. Soc. 1979, 101, 1123-1130.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 1123-1130
    • Wakatsuki, Y.1    Aoki, K.2    Yamazaki, H.3
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  • 157
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    • Reference 10b
    • (f) Reference 10b.
  • 158
    • 4444272111 scopus 로고    scopus 로고
    • note
    • 27b which should render this isomerization easier.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.