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Volumn , Issue 11, 2007, Pages 1780-1784

Gold-catalyzed hydroxy- and alkoxycyclization of functionalized enynes

Author keywords

Alkoxycyclization; Atom economy; Cycloisomerization; Enyne; Gold

Indexed keywords

1,6 ENYNE DERIVATIVE; ACETONE; ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; DIOXANE; GOLD COMPLEX; LIGAND; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

EID: 34447543037     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982570     Document Type: Article
Times cited : (67)

References (43)
  • 1
    • 33845546747 scopus 로고    scopus 로고
    • For representative examples and seminal references, see: a
    • For representative examples and seminal references, see: (a) Hashmi, A. S. H.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7896
    • Hashmi, A.S.H.1    Hutchings, G.J.2
  • 4
    • 29544447401 scopus 로고    scopus 로고
    • Ma, S.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200.
    • (d) Ma, S.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200.
  • 30
    • 18744401616 scopus 로고    scopus 로고
    • For recent intramolecular versions, see: a
    • For recent intramolecular versions, see: (a) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 6962
    • Zhang, L.1    Kozmin, S.A.2
  • 31
    • 34447522081 scopus 로고    scopus 로고
    • See ref. 7e
    • (b) See ref. 7e.
  • 36
    • 34447544528 scopus 로고    scopus 로고
    • I- catalyst precursors.
    • I- catalyst precursors.
  • 37
    • 34447527731 scopus 로고    scopus 로고
    • 6 (30 mol%) was degassed and stirred at r.t. in 14% aq dioxane or in the corresponding alcohol (1.75 mL solvent/mmol of 1). The mixture was filtered through a short pad of Florisil® or silica gel (cyclohexane-EtOAc, 50:50) and the solvents were evaporated under reduced pressure. The crude product was purified if necessary by silica gel flash chromatography (cyclohexane-EtOAc, 90:10) to give the corresponding alcohol or ether.
    • 6 (30 mol%) was degassed and stirred at r.t. in 14% aq dioxane or in the corresponding alcohol (1.75 mL solvent/mmol of 1). The mixture was filtered through a short pad of Florisil® or silica gel (cyclohexane-EtOAc, 50:50) and the solvents were evaporated under reduced pressure. The crude product was purified if necessary by silica gel flash chromatography (cyclohexane-EtOAc, 90:10) to give the corresponding alcohol or ether.
  • 38
    • 34447506534 scopus 로고    scopus 로고
    • Dimethyl 4-(1-Ethoxyphenylmethyl)-3-methylenecyclopentane-1,1- dicarboxylate (2h) Rf, 0.51 (cyclohexane-EtOAc, 80:20, 1H NMR (300 MHz, CDCl3, δ, 1.13 (t, J, 7.0 Hz, 3 H, 2.31-2.44 (m, 2 H, 2.84-3.00 (m, 3 H, 3.24-3.45 (m, 2 H, 3.68 (s, 3 H, 3.74 (s, 3 H, 4.25 (d, J, 6.0 Hz, 1 H, 4.48 (br s, 1 H, 4.91 (br s, 1 H, 7.25-7.34 (m, 5 H, 13C NMR (300 MHz, CDCl3, δ, 15.2 (CH3, 35.4 (CH2, 42.1 (CH2, 49.4 (CH, 52.6 (2 CH3, 58.7 (C, 64.6 (CH2, 83.7 (CH, 108.5 (CH2, 127.2 (2 CH ar, 127.4 (CH ar, 128.1 (2 CH ar, 141.4 (C, 148.6 (C, 172.1 (C, 172.2 (C, MS (DCI/NH3, m/z, 350 [M, NH4, 333 [M, H, HRMS (DCI/CH4, m/z calcd for C19H25O3: 333.1702; found: 333.1703. 3-(1-Ethoxymethylethyl)-4-methylene-N
    • 2: 478.1722; found: 478.1715.
  • 40
    • 34447500530 scopus 로고    scopus 로고
    • Dimethyl 3-Hydroxy-4-methyl-5-methylenecyclohexane-1,1-dicarboxylate (31H) Rf, 0.13 (cyclohexane-EtOAc, 80:20. 1H NMR (300 MHz, CDCl3, δ, 1.14 (d, J, 6.7 Hz, 3 H, 1.81 (dd, J, 13.3, 9.8 Hz, 1 H, 1.95-2.10 (m, 2 H, 2.53-2.61 (m, 2 H, 2.86 (dd, J, 13.6, 9.8 Hz, 1 H, 3.30-3.50 (m, 1 H, 3.47 (s, 3 H, 3.70 (s, 3 H, 4.82 (br s, 1 H, 4.88 (br s, 1 H, 13C NMR (300 MHz, CDCl3, δ, 14.0 (CH3, 38.6 (CH2, 39.7 (CH2, 44.6 (CH, 52.5 (CH3, 52.9 (CH3, 55.9 (C, 73.0 (CH, 111.4 (CH2, 145.0 (C, 170.7 (C, 171.6 (C, MS (DCI/NH3, m/z, 260 [M, NH 4, 243 [M, H, 228 [M, MeOH, NH 4, 211 [M, MeOH, H, HRMS DCI/CH 4, m/z calcd for C12H19O5: 243.1232; found: 24
    • +.


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