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Volumn 44, Issue 10, 2003, Pages 2157-2159

Diastereoselective ruthenium-catalysed cycloisomerisation of diallyllactones: Preparation of exo-methylene spirolactones

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALCOHOL; LACTONE DERIVATIVE; RUTHENIUM DERIVATIVE; TITANIUM TETRACHLORIDE;

EID: 0037416935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00144-8     Document Type: Article
Times cited : (25)

References (21)
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    • Wills, M. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Sainsbury, M., Ed. Polycarbocyclic compounds with separate ring systems, and spiro compounds. Elsevier: Amsterdam, 1994; Vol. 2.
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    • Wills, M.1
  • 8
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    • For palladium-catalysed cycloisomerisations of enynes, see: (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813; (f) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745; (g) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27; (h) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1971, 712.
    • (1998) Synlett , pp. 1
    • Trost, B.M.1    Krische, M.J.2
  • 9
    • 0036522941 scopus 로고    scopus 로고
    • For palladium-catalysed cycloisomerisations of enynes, see: (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813; (f) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745; (g) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27; (h) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1971, 712.
    • (2002) Chem. Rev. , vol.102 , pp. 813
    • Aubert, C.1    Buisine, O.2    Malacria, M.3
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    • For palladium-catalysed cycloisomerisations of enynes, see: (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813; (f) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745; (g) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27; (h) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1971, 712.
    • (1984) J. Chem. Soc., Perkin Trans. 1 , pp. 1745
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    • For palladium-catalysed cycloisomerisations of enynes, see: (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813; (f) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745; (g) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27; (h) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1971, 712.
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  • 12
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    • For palladium-catalysed cycloisomerisations of enynes, see: (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813; (f) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745; (g) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27; (h) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1971, 712.
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 712
    • Bright, A.1    Malone, J.F.2    Nicholson, J.K.3    Powell, J.4    Shaw, B.L.5
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    • -2 mmol) was added to a diallyllactone (1 mmol) solution in ethanol (20 mL). The reaction mixture was then warmed to reflux during 12 h. After removal of the solvent, the crude product was purified by chromatography over silica gel (eluent: petroleum ether/ether (50/50)) to afford spirolactones 2
    • .+, 24), 122 (17), 121 (12), 107 (10), 97 (12), 95 (10), 94 (29), 93 (50), 92 (29), 91 (24), 82 (41), 79 (46), 77 (27), 69 (11), 68 (70), 67 (58), 66 (18), 65 (21), 63 (10), 55 (20), 54 (64), 53 (44), 52 (13), 51 (27), 50 (13), 42 (18), 41 (56), 40 (36), 39 (100).


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