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Volumn 3, Issue 9, 2001, Pages 1265-1267

Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination

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EID: 0000245921     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069352     Document Type: Article
Times cited : (40)

References (34)
  • 21
    • 0028879573 scopus 로고
    • (b) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159.
    • (1995) Tetrahedron , vol.51 , pp. 13103-13159
    • Bunce, R.A.1
  • 25
    • 0001467252 scopus 로고
    • Compounds 4 were prepared by alkylation of 2-alkylfurans: Piancatelli, G.; Scettri, A.; D'Auria, M. Tetrahedron 1980, 36, 661-663. Oxidation of furan ring with peracids: (a) Dominguez, C.; Csáky, A. G.; Plumet, J. Tetrahedron Lett. 1990, 31, 7669-7670.
    • (1980) Tetrahedron , vol.36 , pp. 661-663
    • Piancatelli, G.1    Scettri, A.2    D'Auria, M.3
  • 28
    • 0043122573 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of compounds 6. General Procedure. To a solution of enedione 5 (5 mmol) in acetonitrile (25 mL), the nitroalkane 1 (5 mmol) followed by DBU (5 mmol) were added at room temperature. After the solution was stirred for 6 h at room temperature, the solvent was evaporated at reduced pressure and the residue was purified by column chromatography (hexanes-ethyl acetate 8:2).
  • 33
    • 0042120624 scopus 로고    scopus 로고
    • note
    • Conjugate addition of the nitroalkane to a cyclopentenone, before the elimination of the aldol, is also conceivable. At any event, this dehydration process should occur before the elimination of nitrous acid, since the presence of an acidic hydrogen at C-4 is necessary to afford the exocyclic double bond (see ref 9).


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