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Volumn 71, Issue 17, 2006, Pages 6437-6443

Cationic Rh(I) catalyst in fluorinated alcohol: Mild intramolecular cycloaddition reactions of ester-tethered unsaturated compounds

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTIONS; FLUORINATED ALCOHOLS; RHCODCL2; TETHERED UNSATURATED COMPOUNDS;

EID: 33747440696     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060827x     Document Type: Article
Times cited : (49)

References (54)
  • 4
    • 0003009874 scopus 로고
    • Dauben, W. G., Ed.; John Wiley & Sons: New York
    • Reviews on intramolecular Diels-Alder reactions: (a) Ciganek, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 32, pp 1-374.
    • (1984) Organic Reactions , vol.32 , pp. 1-374
    • Ciganek, E.1
  • 6
    • 0002251962 scopus 로고
    • Curran, D. P., Ed.; JAI Press: Greenwich, CT
    • (c) Roush, W. R. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146.
    • (1990) Advances in Cycloaddition , vol.2 , pp. 91-146
    • Roush, W.R.1
  • 7
    • 0000048482 scopus 로고
    • Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, U.K.
    • (d) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 513-550.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 8
    • 0000719534 scopus 로고    scopus 로고
    • For recent examples on IMDA reactions of ester-tethered triene compounds, see: (a) Jung, M. E.; Huang, A.; Johnson, T. W. Org. Lett. 2000, 2, 1835.
    • (2000) Org. Lett. , vol.2 , pp. 1835
    • Jung, M.E.1    Huang, A.2    Johnson, T.W.3
  • 14
  • 34
    • 33845185652 scopus 로고
    • Ni-catalyzed intramolecular [4+2] cycloaddition reaction of diene-alkene; see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6432
    • Wender, P.A.1    Jenkins, T.E.2
  • 46
    • 0001670201 scopus 로고
    • Thermal IMDA reactions of sorbate derivatives require a very high temperature (200 °C) to give the products; see: (a) Boeckman, R. K., Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789.
    • (1982) J. Org. Chem. , vol.47 , pp. 1789
    • Boeckman Jr., R.K.1    Demko, D.M.2
  • 48
    • 0000515321 scopus 로고
    • Thermal IMDA reactions of 2,4-pentadienyl propiolates are known; see: (a) White, J. D.; Sheldon, B. G. J. Org. Chem. 1981, 46, 2273.
    • (1981) J. Org. Chem. , vol.46 , pp. 2273
    • White, J.D.1    Sheldon, B.G.2
  • 52
    • 0034674966 scopus 로고    scopus 로고
    • As far as we know, the [6+2] cycloaddition with simple vinylcyclobutane has never been successful; see: Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7815
    • Wender, P.A.1    Correa, A.G.2    Sato, Y.3    Sun, R.4
  • 54
    • 33747392537 scopus 로고    scopus 로고
    • note
    • A rhodium chloride complex such as Willkinson's catalyst accelerates the [4+2] cycloaddition of 1,3-diene-8-yne or 1,3,8-triene derivatives in TFE. It has been suggested that TFE enhances the polarizability of the Rh-Cl bond. See, refs 11a and 11d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.