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Volumn 67, Issue 9, 2011, Pages 1609-1616

Gold(I)-catalysed iodoalkoxylation of allenes

Author keywords

Allenes; Ethers; Gold catalysis; Iodoalkoxylation

Indexed keywords

ALLENE DERIVATIVE; GOLD;

EID: 79851511496     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.01.021     Document Type: Article
Times cited : (20)

References (59)
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    • For a review on gold-catalysed reaction of alcohols, see: J. Muzart Tetrahedron 64 2008 5815
    • (2008) Tetrahedron , vol.64 , pp. 5815
    • Muzart, J.1
  • 40
    • 73349134259 scopus 로고    scopus 로고
    • For an example of gold-catalysed intramolecular iodoalkoxylation of allenes, see: B. Gockel, and N. Krause Eur. J. Org. Chem. 2010 311
    • (2010) Eur. J. Org. Chem. , pp. 311
    • Gockel, B.1    Krause, N.2
  • 42
    • 79851515960 scopus 로고    scopus 로고
    • note
    • When the reaction was carried out with either 5 mol % or 15 mol % catalyst added in one portion at the beginning, conversions were ∼70%. A reaction time of 4 h versus 24 h seems to make no difference to the conversion. Therefore, the catalyst was added in three portions as described in order to force the reaction to completion.
  • 45
    • 8444250571 scopus 로고    scopus 로고
    • D. Xu, Z. Lu, Z. Li, and S. Ma Tetrahedron 60 2004 11879 Commercially available allenes were purchased from Sigma-Aldrich
    • (2004) Tetrahedron , vol.60 , pp. 11879
    • Xu, D.1    Lu, Z.2    Li, Z.3    Ma, S.4
  • 46
    • 79851515159 scopus 로고    scopus 로고
    • Reaction with added 3 MS to remove any adventitious water during the reaction results in poor conversions
    • Reaction with added 3 MS to remove any adventitious water during the reaction results in poor conversions.
  • 47
    • 50949117366 scopus 로고    scopus 로고
    • Commercially available from Sigma-Aldrich. For a review on applications of NHC-Au complexes, see: N. Marion, and S.P. Nolan Chem. Soc. Rev. 37 2008 1776
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1776
    • Marion, N.1    Nolan, S.P.2
  • 56
    • 79851510704 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis (<5%), unless otherwise stated. In addition, small amounts of the corresponding hydroalkoxylation products (primary and tertiary allylic ethers, ∼12%) were also observed as by-products using conditions shown in Scheme 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.