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Volumn 130, Issue 50, 2008, Pages 16838-16839

Metal-mediated cyclization of aryl and benzyl glycidyl ethers: A complete scenario

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EID: 58049196944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8062887     Document Type: Article
Times cited : (57)

References (21)
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    • (1996) Org. React , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.S.2
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    • Recent work: (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556.
    • Recent work: (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556.
  • 12
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    • 3 in aza-Prins cyclizations, see: Carballo, R. M.; Ramírez, M. A.; Rodríguez, M. L.; Martín, V. S.; Padrón, J. I. Org. Lett. 2006, 8, 3837-3840.
    • 3 in aza-Prins cyclizations, see: Carballo, R. M.; Ramírez, M. A.; Rodríguez, M. L.; Martín, V. S.; Padrón, J. I. Org. Lett. 2006, 8, 3837-3840.
  • 13
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    • 3: (a) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 5386-5389.
    • 3: (a) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 5386-5389.
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    • 4: (b) Taylor, S. K.; Hockermann, G. L.; Karrick, G. L.; Lyle, S. B.; Schramm, S. B. J. Org. Chem. 1983, 48, 2449.
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    • Metal perchlorates: (d) Chini, M.; Crotti, P.; Flippin, L. A.; Macchia, F. J. Org. Chem. 1990, 55, 4525-4562.
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    • For reviews, see: e, Yamamoto, H, Ed, Wiley-VCH: Weinheim, Germany
    • For reviews, see: (e) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
    • (2006) Lewis Acids in Organic Synthesis
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    • 2O, see: Islas-González, G.; Puigjaner, C.; Vidal-Ferran, A.; Moyano, A.; Riera, A.; Pericàs, M. A. Tetrahedron Lett. 2004, 45, 6337-6341.
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    • 3/3AgOTf catalytic systems have also been tested in the stereospecific and regioselective intermolecular addition of 1,3,5-trimethoxybenzene to (2S,3S)-3-phenylglycidyl methyl ether. The former gave the desired product 7 in 60% yield, whereas the latter was less active (ca. 40%; see SI for details). Further studies concerning related intermolecular addition are in course.
    • 3/3AgOTf catalytic systems have also been tested in the stereospecific and regioselective intermolecular addition of 1,3,5-trimethoxybenzene to (2S,3S)-3-phenylglycidyl methyl ether. The former gave the desired product 7 in 60% yield, whereas the latter was less active (ca. 40%; see SI for details). Further studies concerning related intermolecular addition are in course.


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