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Volumn 51, Issue 38, 2010, Pages 5064-5067

Reversible aqueous metathesis reactions for potential application in dynamic combinatorial chemistry

Author keywords

Allyl sulfides; Aqueous metathesis; Dynamic combinatorial chemistry; Reversible metathesis

Indexed keywords

ALKENE; ALLYL COMPOUND; NAPHTHALIMIDE DERIVATIVE;

EID: 78549273321     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.105     Document Type: Article
Times cited : (21)

References (53)
  • 1
    • 0032820242 scopus 로고    scopus 로고
    • For major reviews, see
    • For major reviews, see: (a) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455-2463;
    • (1999) Chem. Eur. J. , vol.5 , pp. 2455-2463
    • Lehn, J.-M.1
  • 13
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    • Kazmierski, W. M., Ed.; Humana Press: Totowa, NJ
    • Henninger, T. C.; Wipf, P.. In Peptidomimetics Protocols; Kazmierski, W. M., Ed.; Humana Press: Totowa, NJ, 1999; Vol. 23, pp 125-136.
    • (1999) Peptidomimetics Protocols , vol.23 , pp. 125-136
    • Henninger, T.C.1    Wipf, P.2
  • 42
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    • This strategy is analogous to the disulfide DCL design employed by Nielsen and Ulven outlined in Ref.2b
    • This strategy is analogous to the disulfide DCL design employed by Nielsen and Ulven outlined in Ref.2b.
  • 43
    • 85030586024 scopus 로고    scopus 로고
    • Typical procedure: Hoveyda-Grubbs second generation catalyst (1.5 mg, 2.5 μmol) was dissolved in t-BuOH (0.25 mL) by repeated sonication and vortexing. The resultant clear green solution was added to a stirred mixture of the allyl sulfide (41 μmol), allyl alcohol (7) (57 μL, 0.82 mmol), t-BuOH (0.25 mL) and in-house Milli-Q® water (0.5 mL) at 32°C, and the mixture was stirred at 32°C for 1 h. During this time the reaction mixture changed from a green color to a yellow color within a few minutes, then more gradually to a brown/black color. A second solution of Hoveyda-Grubbs second generation catalyst (1.5 mg, 2.5 μmol) in t-BuOH (0.25 mL) was added followed by Milli-Q® water (0.25 mL), and the mixture was stirred at 32°C for 1.5 h. The mixture was concentrated to give the crude product which was purified by chromatography
    • Typical procedure: Hoveyda-Grubbs second generation catalyst (1.5 mg, 2.5 μmol) was dissolved in t-BuOH (0.25 mL) by repeated sonication and vortexing. The resultant clear green solution was added to a stirred mixture of the allyl sulfide (41 μmol), allyl alcohol (7) (57 μL, 0.82 mmol), t-BuOH (0.25 mL) and in-house Milli-Q® water (0.5 mL) at 32°C, and the mixture was stirred at 32°C for 1 h. During this time the reaction mixture changed from a green color to a yellow color within a few minutes, then more gradually to a brown/black color. A second solution of Hoveyda-Grubbs second generation catalyst (1.5 mg, 2.5 μmol) in t-BuOH (0.25 mL) was added followed by Milli-Q® water (0.25 mL), and the mixture was stirred at 32°C for 1.5 h. The mixture was concentrated to give the crude product which was purified by chromatography.
  • 45
    • 85030589126 scopus 로고    scopus 로고
    • note
    • + requires m/z 247.0905, found 247.0880.
  • 47
    • 84902431981 scopus 로고    scopus 로고
    • Constable, E. C., Dilworth, J. R., Eds Elsevier Pergamon: San Diego
    • Housecroft, C. E.. In Comprehensive Coordination Chemistry II; Constable, E. C., Dilworth, J. R., Eds.; Elsevier Pergamon: San Diego, 2004; Vol. 5, pp 555-731.
    • (2004) Comprehensive Coordination Chemistry II , vol.5 , pp. 555-731
    • Housecroft, C.E.1
  • 51
    • 85030577094 scopus 로고    scopus 로고
    • note
    • +], relative area 58%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.