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Volumn , Issue 4, 2006, Pages 571-574

A facile and stereoselective synthesis of unsymmetrical diallylsulfides via indium-promoted one-pot reaction of Baylis-Hillman acetates, sodium thiosulfate, and allyl bromide

Author keywords

Allyl bromide; Baylis Hillman acetates; Diallylsulfides; Indium; Stereoselective

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL BROMIDE; ALLYL COMPOUND; ALLYL SULFIDE; INDIUM; SODIUM THIOSULFATE; UNCLASSIFIED DRUG;

EID: 33644996502     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-932496     Document Type: Article
Times cited : (23)

References (59)
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    • Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: New York, Chap. 3.10
    • For reviews, see: (a) Markó, I. E. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: New York, 1991, Chap. 3.10.
    • (1991) Comprehensive Organic Synthesis , vol.3
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    • For reviews, see: (a) Ciganek, E. Org. React. 1997, 57, 201.
    • (1997) Org. React. , vol.57 , pp. 201
    • Ciganek, E.1
  • 46
    • 0000632582 scopus 로고
    • Some allyl sulfide analogues prepared from Baylis-Hillman alcohols or Baylis-Hillman bromides by other approaches have been previously reported in literature, see: (a) Calò, V.; Lopez, L.; Pesce, G. J. Organomet. Chem. 1988, 353, 405.
    • (1988) J. Organomet. Chem. , vol.353 , pp. 405
    • Calò, V.1    Lopez, L.2    Pesce, G.3
  • 51
    • 33644992802 scopus 로고    scopus 로고
    • note
    • 2O (0.25 g, 1 mmol), Baylis-Hillman acetate 1 (1 mmol), and anhyd MeOH (15 mL). The mixture was stirred at r.t. for 4-8 h. Then, to the resultant mixture was added silica gel powder (2.0 g). After evaporation of the solvent, the silica gel-absorbed crude product was loaded to chromatography column for further purification using MeOH-EtOAc (1:1) as eluent.
  • 52
    • 0001420970 scopus 로고
    • 1H NMR spectrum of a trisubstituted alkene the β-vinylic proton, cis and trans to the ester group are known to resonate at δ = 7.5 ppm and δ = 6.5 ppm, respectively, when alkene is substituted by an aryl group; while the same proton cis and trans to an ester group appears at δ = 6.8 ppm and δ = 5.7 ppm, respectively, when substituted by an alkyl one. See: (a) Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385.
    • (1984) J. Org. Chem. , vol.49 , pp. 3385
    • Larson, G.L.1    De Kaifer, C.F.2    Seda, R.3    Torres, L.E.4    Ramirez, J.R.5
  • 56
    • 33645008290 scopus 로고    scopus 로고
    • note
    • 2: C, 42.57; H, 3.57. Found: C, 42.89; H, 3.65.
  • 57
    • 24044470646 scopus 로고    scopus 로고
    • Li, C. J. Chem. Rev. 2005, 105, 3095.
    • (2005) Chem. Rev. , vol.105 , pp. 3095
    • Li, C.J.1
  • 58
    • 33644992801 scopus 로고    scopus 로고
    • note
    • 4. After evaporation of solvent, the residue was purified by chromatography using cyclohexane-EtOAc (6:1) as eluent.
  • 59
    • 33644996185 scopus 로고    scopus 로고
    • note
    • 3S: C, 64.72; H, 6.52. Found: C, 64.96; H, 6.62.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.