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Volumn 4, Issue 17, 2002, Pages 2817-2819

Copper(II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature

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EID: 19044364173     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025997k     Document Type: Article
Times cited : (102)

References (33)
  • 4
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    • For a review, see: Smith, J. G. Synthesis 1984, 629-656.
    • (1984) Synthesis , pp. 629-656
    • Smith, J.G.1
  • 7
    • 0035138531 scopus 로고    scopus 로고
    • and references therein
    • (c) Salomon, C. J. Synlett 2001, 65-68 and references therein.
    • (2001) Synlett , pp. 65-68
    • Salomon, C.J.1
  • 23
    • 0042004435 scopus 로고    scopus 로고
    • note
    • All the reported ring-opened epoxide derivatives gave analytical and spectroscopic data in agreement with the proposed structures.
  • 24
    • 12444262104 scopus 로고
    • Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon: Oxford, Chapter 5
    • Lewars, E. G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon: Oxford, 1984; Vol. 7; Chapter 5, pp 100-113.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.7 , pp. 100-113
    • Lewars, E.G.1
  • 25
    • 0000244529 scopus 로고
    • The fact that 15 reacts under these conditions establishes a marked contrast with the previously noticed unreactivity of alkyl-substituted terminal epoxides in copper(II)-catalyzed opening reaction in the presence of acetone at 60 °C; see: Hanzlik, R. P.; Leinwetter, M. J. Org. Chem. 1978, 43, 438-440.
    • (1978) J. Org. Chem. , vol.43 , pp. 438-440
    • Hanzlik, R.P.1    Leinwetter, M.2
  • 28
    • 0001301294 scopus 로고
    • For the preparation of 22 and studies on its ring opening by water, see: Brown, H. C.; Suzuki, A. J. Am. Chem. Soc. 1967, 89, 1933-1941.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1933-1941
    • Brown, H.C.1    Suzuki, A.2
  • 32
    • 0034833453 scopus 로고    scopus 로고
    • For the first examples of intermolecular kinetic resolution of epoxides with alcohols catalyzed by metal complexes, see: Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688. For related recent work, see: Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2687-2688
    • Ready, J.M.1    Jacobsen, E.N.2
  • 33
    • 0037091011 scopus 로고    scopus 로고
    • For the first examples of intermolecular kinetic resolution of epoxides with alcohols catalyzed by metal complexes, see: Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688. For related recent work, see: Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1374-1377
    • Ready, J.M.1    Jacobsen, E.N.2


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