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Volumn 4, Issue 11, 2002, Pages 1823-1826

Enantioenriched Dihydropyrones from β-Lactone Templates

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; PYRONE DERIVATIVE;

EID: 0037198746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025607u     Document Type: Article
Times cited : (27)

References (37)
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    • and references therein
    • (h) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588 and references therein.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3558-3588
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  • 29
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    • Ref 5b
    • (h) Ref 5b.
  • 30
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    • For the aldol polymerization of acetaldehyde enolate equivalents, see: (a) Murahashi, S.; Nozakura, S.; Sumi, M. J. Polym. Sci., Polym. Lett. 1965, 3, 245-249. (b) Nozakura, S.-I.; Ishihara, S.; Inaba, Y.; Matsumura, K.; Murahashi, S. J. Polym. Sci. 1973, 11, 1053-1067. (c) Sogah, D. Y.; Webster, O. W. In Recent Advances in Mechanistic and Synthetic Aspects of Polymerization; Fontanille, M., Guyot, A., Eds.; D. Reidel: Dordrecht, The Netherlands, 1987; pp 61-72. (d) Charleux, B.; Pichot, C. Polymer 1993, 34, 195-203.
    • (1965) J. Polym. Sci., Polym. Lett. , vol.3 , pp. 245-249
    • Murahashi, S.1    Nozakura, S.2    Sumi, M.3
  • 31
    • 0015629114 scopus 로고
    • For the aldol polymerization of acetaldehyde enolate equivalents, see: (a) Murahashi, S.; Nozakura, S.; Sumi, M. J. Polym. Sci., Polym. Lett. 1965, 3, 245-249. (b) Nozakura, S.-I.; Ishihara, S.; Inaba, Y.; Matsumura, K.; Murahashi, S. J. Polym. Sci. 1973, 11, 1053-1067. (c) Sogah, D. Y.; Webster, O. W. In Recent Advances in Mechanistic and Synthetic Aspects of Polymerization; Fontanille, M., Guyot, A., Eds.; D. Reidel: Dordrecht, The Netherlands, 1987; pp 61-72. (d) Charleux, B.; Pichot, C. Polymer 1993, 34, 195-203.
    • (1973) J. Polym. Sci. , vol.11 , pp. 1053-1067
    • Nozakura, S.-I.1    Ishihara, S.2    Inaba, Y.3    Matsumura, K.4    Murahashi, S.5
  • 32
    • 0343071172 scopus 로고
    • Fontanille, M., Guyot, A., Eds.; D. Reidel: Dordrecht, The Netherlands
    • For the aldol polymerization of acetaldehyde enolate equivalents, see: (a) Murahashi, S.; Nozakura, S.; Sumi, M. J. Polym. Sci., Polym. Lett. 1965, 3, 245-249. (b) Nozakura, S.-I.; Ishihara, S.; Inaba, Y.; Matsumura, K.; Murahashi, S. J. Polym. Sci. 1973, 11, 1053-1067. (c) Sogah, D. Y.; Webster, O. W. In Recent Advances in Mechanistic and Synthetic Aspects of Polymerization; Fontanille, M., Guyot, A., Eds.; D. Reidel: Dordrecht, The Netherlands, 1987; pp 61-72. (d) Charleux, B.; Pichot, C. Polymer 1993, 34, 195-203.
    • (1987) Recent Advances in Mechanistic and Synthetic Aspects of Polymerization , pp. 61-72
    • Sogah, D.Y.1    Webster, O.W.2
  • 33
    • 0027856960 scopus 로고
    • For the aldol polymerization of acetaldehyde enolate equivalents, see: (a) Murahashi, S.; Nozakura, S.; Sumi, M. J. Polym. Sci., Polym. Lett. 1965, 3, 245-249. (b) Nozakura, S.-I.; Ishihara, S.; Inaba, Y.; Matsumura, K.; Murahashi, S. J. Polym. Sci. 1973, 11, 1053-1067. (c) Sogah, D. Y.; Webster, O. W. In Recent Advances in Mechanistic and Synthetic Aspects of Polymerization; Fontanille, M., Guyot, A., Eds.; D. Reidel: Dordrecht, The Netherlands, 1987; pp 61-72. (d) Charleux, B.; Pichot, C. Polymer 1993, 34, 195-203.
    • (1993) Polymer , vol.34 , pp. 195-203
    • Charleux, B.1    Pichot, C.2
  • 36
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    • note
    • β-Keto hydrazone intermediates 6 can be isolated and purified by column chromatography; however, crude β-keto hydrazones emerging from the β-lactone ring openings were routinely used in the subsequent cyclization reactions.
  • 37
    • 0442263828 scopus 로고    scopus 로고
    • note
    • 4), filtered, and concentrated. The resulting residue was dissolved in THF (10 mL), and amberlyst-15 acidic resin (500 mg) was added; the reaction was heated at reflux for 3 h. Upon cooling to ambient temperature, the mixture was filtered, concentrated, and purified by flash chromatography.


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