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Volumn 72, Issue 5, 2007, Pages 1859-1862

Mechanistic insights into the palladiumII-catalyzed hydroxyalkoxylation of 2-allylphenols

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED OXIDATION; HYDROXYALKOXYLATION; OXIRANE;

EID: 33847659571     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062491x     Document Type: Article
Times cited : (48)

References (35)
  • 3
    • 33644933015 scopus 로고    scopus 로고
    • 2[(-)-sparteine] as the catalyst: (a) Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 2794-2795.
    • 2[(-)-sparteine] as the catalyst: (a) Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 2794-2795.
  • 5
    • 37049134062 scopus 로고    scopus 로고
    • II-catalyzed isomerization of allylphenol, see: (a) Golborn, P.; Scheimann, F. J. Chem. Soc., Perkin Trans. 1 1973, 2870-2875.
    • II-catalyzed isomerization of allylphenol, see: (a) Golborn, P.; Scheimann, F. J. Chem. Soc., Perkin Trans. 1 1973, 2870-2875.
  • 8
    • 33847612974 scopus 로고    scopus 로고
    • ref. 2
    • (d) ref. 2.
  • 9
    • 33847670626 scopus 로고    scopus 로고
    • 2O/MeOH solution, led to 2-((E)-prop-1-enyl)-6-methylphenol (17%), 2-(1,2-dihydroxypropyl)-6-methylphenol (15%), and 2-(2-hydroxy-1-methoxypropyl)-6-methylphenol (30%).
    • 2O/MeOH solution, led to 2-((E)-prop-1-enyl)-6-methylphenol (17%), 2-(1,2-dihydroxypropyl)-6-methylphenol (15%), and 2-(2-hydroxy-1-methoxypropyl)-6-methylphenol (30%).
  • 10
    • 33847657980 scopus 로고    scopus 로고
    • See Supporting Information for the determination of the syn and anti structures via the synthesis of 2-(2,2,5-trimethyl-1,3-dioxolan-4- yl)phenol and 1H NMR analysis
    • 1H NMR analysis.
  • 17
    • 33847679564 scopus 로고    scopus 로고
    • Bn has also been prepared from 4 in two steps (benzylation followed by epoxidation), but this procedure was less convenient.
    • Bn has also been prepared from 4 in two steps (benzylation followed by epoxidation), but this procedure was less convenient.
  • 18
    • 0032473894 scopus 로고    scopus 로고
    • The Pd-catalyzed hydrogenolysis of epoxides leads usually to the corresponding alcohols even in alcoholic solvents Schultze, L. M, Chapman, H. H, Dubree, N. J. P, Jones, R. J, Kent, K. M, Lee, T. T, Louie, M. S, Postich, M. J, Prisbe, E. J, Rohloff, J. C, Yu, R. H. Tetrahedron Lett. 1998, 39, 1853-1856
    • The Pd-catalyzed hydrogenolysis of epoxides leads usually to the corresponding alcohols even in alcoholic solvents (Schultze, L. M.; Chapman, H. H.; Dubree, N. J. P.; Jones, R. J.; Kent, K. M.; Lee, T. T.; Louie, M. S.; Postich, M. J.; Prisbe, E. J.; Rohloff, J. C.; Yu, R. H. Tetrahedron Lett. 1998, 39, 1853-1856),
  • 19
    • 0033532534 scopus 로고    scopus 로고
    • but the formation of 2-methoxy-2-phenylethanol from styrene oxide under such conditions is documented (Sajiki, H.; Hattori, K.; Hirota, H. Chem. Commun. 1999, 1041-1042).
    • but the formation of 2-methoxy-2-phenylethanol from styrene oxide under such conditions is documented (Sajiki, H.; Hattori, K.; Hirota, H. Chem. Commun. 1999, 1041-1042).
  • 20
    • 0013683253 scopus 로고
    • For Lewis acid catalyzed alcoholysis of epoxides, see: a
    • For Lewis acid catalyzed alcoholysis of epoxides, see: (a) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Synlett 1992, 673-676.
    • (1992) Synlett , pp. 673-676
    • Chini, M.1    Crotti, P.2    Gardelli, C.3    Macchia, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.