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Volumn 9, Issue 6, 2007, Pages 1028-1035

Skeletal diversity in small-molecule synthesis using ligand-controlled catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ETHER DERIVATIVE; LIGAND; ORGANOSILICON DERIVATIVE; PALLADIUM; PHOSPHINE; PHOSPHINE DERIVATIVE;

EID: 36649005330     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc7001028     Document Type: Article
Times cited : (11)

References (48)
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    • For mechanistic references on aristolochene and pentalenene synthases, respectively: a
    • For mechanistic references on aristolochene and pentalenene synthases, respectively: (a) Rising, K. A.; Starks, C. M.; Noel, J. P.; Chappell, J. J. Am. Chem. Soc. 2000, 122, 1861-1866.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 1861-1866
    • Rising, K.A.1    Starks, C.M.2    Noel, J.P.3    Chappell, J.4
  • 5
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    • (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 7
    • 33644651861 scopus 로고    scopus 로고
    • For selected examples of catalyst/ligand-control of skeletal diversity, see: a
    • For selected examples of catalyst/ligand-control of skeletal diversity, see: (a) Vitale, M.; Lecourt, T.; Sheldon, C. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2006, 128, 2524-2525.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 2524-2525
    • Vitale, M.1    Lecourt, T.2    Sheldon, C.G.3    Aggarwal, V.K.4
  • 11
    • 3042799070 scopus 로고    scopus 로고
    • For examples of reagent-based approaches to skeletal diversity differentiating processes, see Burke, M. D, Schreiber, S. L. Angew. Chem, Int. Ed. 2004, 43, 46-58, and references therein
    • For examples of reagent-based approaches to skeletal diversity (differentiating processes), see Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58, and references therein.
  • 24
    • 0347983789 scopus 로고    scopus 로고
    • For similar examples of diyne cyclodimerization, see
    • (a) For similar examples of diyne cyclodimerization, see Kotha, S.; Brahmachary, E. J. Organomet. Chem. 2004, 689, 158-163.
    • (2004) J. Organomet. Chem , vol.689 , pp. 158-163
    • Kotha, S.1    Brahmachary, E.2
  • 30
    • 36649037489 scopus 로고    scopus 로고
    • a values stronger than AcOH resulted in cleavage of the silyl ether.
    • a values stronger than AcOH resulted in cleavage of the silyl ether.
  • 31
    • 0001342781 scopus 로고    scopus 로고
    • For early mechanistic studies consistent with Pd(II) as the active catalyst, see Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161-3163.
    • For early mechanistic studies consistent with Pd(II) as the active catalyst, see Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161-3163.
  • 32
    • 0028266112 scopus 로고    scopus 로고
    • A reductive cyclization-alkylation of 1,6-enynes where ring size is controlled by choice of ligand (dppp versus dmppp) has been described. Trost, B. M.; Zhi, L.; Imi, K. Tetrahedron Lett. 1994, 35, 1361-1364.
    • A reductive cyclization-alkylation of 1,6-enynes where ring size is controlled by choice of ligand (dppp versus dmppp) has been described. Trost, B. M.; Zhi, L.; Imi, K. Tetrahedron Lett. 1994, 35, 1361-1364.
  • 35
    • 0001586814 scopus 로고    scopus 로고
    • In several reported cases, catalysts formed in the absence of phosphine ligands give optimal results. Ligandless conditions applied to the silyl ether substrates routinely gave complex product mixtures, suggesting a balance between catalyst stability and activity is necessary for this substrate class. See Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651-654.
    • In several reported cases, catalysts formed in the absence of phosphine ligands give optimal results. Ligandless conditions applied to the silyl ether substrates routinely gave complex product mixtures, suggesting a balance between catalyst stability and activity is necessary for this substrate class. See Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651-654.
  • 36
    • 36649037286 scopus 로고    scopus 로고
    • Alkynes bearing electron-deficient substituents should be less reactive toward the key hydridopalladium carboxlate species
    • Alkynes bearing electron-deficient substituents should be less reactive toward the key hydridopalladium carboxlate species.
  • 37
    • 3543125474 scopus 로고    scopus 로고
    • For an example of cycloaddition starting from a 1-substituted oxasilacyclopentene, see
    • For an example of cycloaddition starting from a 1-substituted oxasilacyclopentene, see: Clark, T. B.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9522-9523.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 9522-9523
    • Clark, T.B.1    Woerpel, K.A.2
  • 38
    • 4644352301 scopus 로고    scopus 로고
    • For an example of an enyne metathesis sequence yielding a mixture of the exo and endo adducts, see reference 19e. Maifeld, S. V.; Miller, R. L.; Lee, D. J. Am. Chem. Soc. 2004, 126, 12228-12229.
    • (a) For an example of an enyne metathesis sequence yielding a mixture of the exo and endo adducts, see reference 19e. Maifeld, S. V.; Miller, R. L.; Lee, D. J. Am. Chem. Soc. 2004, 126, 12228-12229.
  • 46
    • 36649033219 scopus 로고    scopus 로고
    • Tricyclic silacycles of type IX were found to be unstable to silica gel and were chromatographed through 20 micron powdered cellulose. Silacyclic dienes of type V were unreactive towards most dienophiles at temperatures that did not incur decomposition of the diene.
    • Tricyclic silacycles of type IX were found to be unstable to silica gel and were chromatographed through 20 micron powdered cellulose. Silacyclic dienes of type V were unreactive towards most dienophiles at temperatures that did not incur decomposition of the diene.


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