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Volumn , Issue 21, 2000, Pages 3645-3654

Parallel solution-phase syntheses of functionalised bicyclo[2.2.2]octanes: Generation of a library using orchestrated multistep sequences of polymer-supported reagents and sequesterants

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHROMATOGRAPHY; MOLECULAR WEIGHT; SYNTHESIS (CHEMICAL);

EID: 85047678433     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003129l     Document Type: Article
Times cited : (24)

References (72)
  • 44
    • 0034152278 scopus 로고    scopus 로고
    • Preliminary results have been published: S. V. Ley and A. Massi, J. Comb. Chem., 2000, 2, 104.
    • (2000) J. Comb. Chem. , vol.2 , pp. 104
    • Ley, S.V.1    Massi, A.2
  • 49
    • 33645916937 scopus 로고    scopus 로고
    • tert-Bulyl cinnamate 9e was prepared by reacting trans-cinnamic acid with an excess of 2-methylpropene in the presence of catalytic sulfuric acid (DCM, -25 °C, 2 h)
    • tert-Bulyl cinnamate 9e was prepared by reacting trans-cinnamic acid with an excess of 2-methylpropene in the presence of catalytic sulfuric acid (DCM, -25 °C, 2 h).
  • 50
    • 33645926267 scopus 로고    scopus 로고
    • The quenching-sequestering action of Amberlyst A15 is monitored by the change of colour of the reaction mixture, from red-orange to colourless
    • The quenching-sequestering action of Amberlyst A15 is monitored by the change of colour of the reaction mixture, from red-orange to colourless.
  • 51
    • 33645897240 scopus 로고    scopus 로고
    • 3-(3-Mercaptophenyl)propanamidomethyl polystyrene (PS-thio-phenol) was purchased from Argonaut Technologies. Since the resin is predominantly the disulfide form, the resin is first treated with a 0.7 M tributylphosphine solution followed by washing with deoxygenated THF
    • 3-(3-Mercaptophenyl)propanamidomethyl polystyrene (PS-thio-phenol) was purchased from Argonaut Technologies. Since the resin is predominantly the disulfide form, the resin is first treated with a 0.7 M tributylphosphine solution followed by washing with deoxygenated THF.
  • 52
    • 84982386784 scopus 로고
    • Macroporous triethylammonium methylpolystyrene carbonate resin (MP-carbonate) was purchased from Argonaut Technologies. The triethylammonium carbonate resin has been prepared and used in synthesis; G. Cardillo, M. Orena, G. Porzin and S. Sandri, Synthesis, 1981, 793.
    • (1981) Synthesis , pp. 793
    • Cardillo, G.1    Orena, M.2    Porzin, G.3    Sandri, S.4
  • 53
    • 33645953219 scopus 로고    scopus 로고
    • The endo-exo ratio in compounds 10-13 was at least 24:1 (GC analysis)
    • The endo-exo ratio in compounds 10-13 was at least 24:1 (GC analysis).
  • 56
    • 33645943944 scopus 로고    scopus 로고
    • -1 and purchased from Fluka
    • -1 and purchased from Fluka.
  • 57
    • 33645945964 scopus 로고    scopus 로고
    • Compounds 22-24 were obtained in lower yield and purity when the reaction was performed under the same conditions but in the absence of PS-BEMP
    • Compounds 22-24 were obtained in lower yield and purity when the reaction was performed under the same conditions but in the absence of PS-BEMP.
  • 59
    • 0029813591 scopus 로고    scopus 로고
    • Other approaches to amine libraries using polymer-supported reagents are reported in (a) S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 1996, 118, 8977
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8977
    • Kobayashi, S.1    Nagayama, S.2
  • 62
    • 33645939862 scopus 로고    scopus 로고
    • note
    • 2-Thenylmethylamine 25c was purchased from Acres. 2-Amino-methyl-3-chlorodiphenyl ether 25d and 4-(2-aminoethylthio)-2-(trifluoromethyl)quinoline 25e were purchased from Maybridge. Piperonylamine 25f was purchased from Aldrich.
  • 63
    • 33645945187 scopus 로고    scopus 로고
    • note
    • IH NMR analysis) and ∼4:1 in the tetrahydrofurfuryl series (GC analysis).
  • 64
    • 33645918890 scopus 로고    scopus 로고
    • 4-Benzyloxybenzaldehyde polystyrene (Aldehyde Wang resin) was purchased from Novabiochem
    • 4-Benzyloxybenzaldehyde polystyrene (Aldehyde Wang resin) was purchased from Novabiochem.
  • 65
    • 33645951896 scopus 로고    scopus 로고
    • note
    • 4-(Trifluoromethyl)benzyl bromide 38a and 4-fluorobenzyl bromide 38b were purchased from Aldrich. 6-(Bromomethyl)-4-chloro-2-(trifluoromethyl)quinoline 38c and 4-(4-bromomethylphenyl)-1,2,3-thiadiazole 38d were purchased from Maybridge.
  • 66
    • 33645950982 scopus 로고    scopus 로고
    • Aminomethylated polystyrene (AM resin) was purchased from Novabiochem
    • Aminomethylated polystyrene (AM resin) was purchased from Novabiochem.
  • 67
    • 33645921221 scopus 로고    scopus 로고
    • Methyl isocyanate resin was purchased from Novabiochem
    • Methyl isocyanate resin was purchased from Novabiochem.
  • 69
    • 33645907752 scopus 로고    scopus 로고
    • Prolonged reaction time leads to lower yield of 52a,b, S4a,b and 56a,b (naphthalenemethyl series) due to acidic cleavage of the naphthalenemethyl group
    • Prolonged reaction time leads to lower yield of 52a,b, S4a,b and 56a,b (naphthalenemethyl series) due to acidic cleavage of the naphthalenemethyl group.
  • 70
    • 33645918188 scopus 로고    scopus 로고
    • Triphenylphosphine on polystyrene (crosslinked with 2% DVB) was purchased from Fluka
    • Triphenylphosphine on polystyrene (crosslinked with 2% DVB) was purchased from Fluka.
  • 71
    • 33645928643 scopus 로고    scopus 로고
    • 3N is essential to liberate the amino function of L-valine tert-butyl ester hydrochloride 58d which reacts smoothly with an excess of acyl bromide
    • 3N is essential to liberate the amino function of L-valine tert-butyl ester hydrochloride 58d which reacts smoothly with an excess of acyl bromide.
  • 72
    • 33645940817 scopus 로고    scopus 로고
    • Available from IST catalogue (international sorbent technology)
    • Available from IST catalogue (international sorbent technology).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.