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Volumn 10, Issue 9, 2008, Pages 1867-1870

Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into α,ß-unsaturated carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; GOLD; MOLYBDENUM; PROPANOL; PROPARGYL ALCOHOL;

EID: 48849090018     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800596c     Document Type: Article
Times cited : (128)

References (31)
  • 3
  • 20
    • 58149201726 scopus 로고    scopus 로고
    • We found that the rearrangement of the corresponding ethoxyethy-nyl derivative using AgOTf (1 mol , alone was completed at room temperature for 0.5 h; however, that of lq with AgOTf 2 mol , alone gave 2q in less than 5% NMR yields. Thus, the trimetallic catalytic system was revealed to be highly effective for less activated alkynes. For details, see Supporting Information
    • We found that the rearrangement of the corresponding ethoxyethy-nyl derivative using AgOTf (1 mol %) alone was completed at room temperature for 0.5 h; however, that of lq with AgOTf (2 mol %) alone gave 2q in less than 5% NMR yields. Thus, the trimetallic catalytic system was revealed to be highly effective for less activated alkynes. For details, see Supporting Information.
  • 23
    • 0000851696 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon, Oxford
    • Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon, Oxford, 1991; Vol. 2, p, 133.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133
    • Heathcock, C.H.1
  • 26
    • 58149195579 scopus 로고    scopus 로고
    • 2CN, followed by reduction (and oxidation). For the recent use of this approach, see:
    • 2CN, followed by reduction (and oxidation). For the recent use of this approach, see:
  • 28
    • 33846538644 scopus 로고    scopus 로고
    • Alternative condensation reactions using acetaldehyde equivalents have also been developed; however, they produce wastes and/or byproducts
    • (b) Maddess, M. L.; Tackett, M. N.; Watanabe, H.; Brennan, P. E.; Spilling, C. D.; Scott, J. S.; Osborn, D. P.; Ley, S. Angew. Chem., Int. Ed 2007,46,591. Alternative condensation reactions using acetaldehyde equivalents have also been developed; however, they produce wastes and/or byproducts.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 591
    • Maddess, M.L.1    Tackett, M.N.2    Watanabe, H.3    Brennan, P.E.4    Spilling, C.D.5    Scott, J.S.6    Osborn, D.P.7    Ley, S.8
  • 31
    • 58149188654 scopus 로고    scopus 로고
    • 2O 10:1) to give 5-phenyl-1-penten-3-one 2a (93 mg, 93%) as a colorless oil.
    • 2O 10:1) to give 5-phenyl-1-penten-3-one 2a (93 mg, 93%) as a colorless oil.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.