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Volumn 65, Issue 9, 2009, Pages 1809-1832

Gold-catalyzed cycloisomerizations of ene-ynamides

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; CYCLOBUTANONE DERIVATIVE; GOLD; NITROGEN; PYRROLIDINE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

EID: 58949090317     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.108     Document Type: Article
Times cited : (71)

References (111)
  • 15
  • 16
    • 58949103935 scopus 로고    scopus 로고
    • For selected references on the cycloisomerization of enynes, see:
    • For selected references on the cycloisomerization of enynes, see:
  • 31
  • 34
    • 58949090584 scopus 로고    scopus 로고
    • For reviews on gold-catalysis including not solely enyne cycloisomerizations, see:
    • For reviews on gold-catalysis including not solely enyne cycloisomerizations, see:
  • 48
  • 49
  • 51
    • 58949091515 scopus 로고    scopus 로고
    • For a special issue devoted to the chemistry of ynamides, see:
    • For a special issue devoted to the chemistry of ynamides, see:. Tetrahedron 62 (2006)
    • (2006) Tetrahedron , vol.62
  • 52
    • 58949095872 scopus 로고    scopus 로고
    • For recent references concerning the gold-catalyzed synthesis of oxazolones from N-alkynylcarbamates, see:
    • For recent references concerning the gold-catalyzed synthesis of oxazolones from N-alkynylcarbamates, see:
  • 59
    • 33750194180 scopus 로고    scopus 로고
    • For a preliminary communication, see:
    • For a preliminary communication, see:. Couty S., Meyer C., and Cossy J. Angew. Chem., Int. Ed. 45 (2006) 6726-6730
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 6726-6730
    • Couty, S.1    Meyer, C.2    Cossy, J.3
  • 66
    • 58949087626 scopus 로고    scopus 로고
    • note
    • 10
  • 72
    • 0032417755 scopus 로고    scopus 로고
    • Alkenyl iodide 23 was prepared by hydrozirconation of the THP ether derived from but-3-yn-1-ol followed by iodinolysis, see:
    • Alkenyl iodide 23 was prepared by hydrozirconation of the THP ether derived from but-3-yn-1-ol followed by iodinolysis, see:. Yokomatsu T., Abe H., Sato M., Suemune K., Kihara T., Soeda S., Shimeno H., and Shibuya S. Bioorg. Med. Chem. 66 (1998) 2495-2505
    • (1998) Bioorg. Med. Chem. , vol.66 , pp. 2495-2505
    • Yokomatsu, T.1    Abe, H.2    Sato, M.3    Suemune, K.4    Kihara, T.5    Soeda, S.6    Shimeno, H.7    Shibuya, S.8
  • 82
    • 58949090583 scopus 로고    scopus 로고
    • note
    • 4o,p led to similar results in terms of yield and diastereoselectivity.
  • 83
    • 58949098520 scopus 로고    scopus 로고
    • note
    • 3, MeOH, reflux), which led to a 50:50 mixture of diastereomers.
  • 85
    • 58949094624 scopus 로고    scopus 로고
    • note
    • The relative configuration of 46 has been indicated for the sake of clarity but the actual sense of 1,2-stereochemical induction for 1,6-ene-ynamides substituted at the β position of the nitrogen atom was only ascertained later with ene-ynamide 68 bearing a propargylic alcohol moiety (see Section 2.3).
  • 87
    • 0003417469 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon, Oxford pp 1047-1082
    • Hiemstra H., and Speckamp W.N. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford pp 1047-1082
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Hiemstra, H.1    Speckamp, W.N.2
  • 90
    • 58949089658 scopus 로고    scopus 로고
    • note
    • The gold-catalyzed cycloisomerization of 1,6-ene-ynamide 37 may generate dienamide 92 as a by-product. Hydrolysis of the latter compound may produce the β-dimethylphenylsilyl enone 49 through an intermediate allenamide 93.{A figure is presented}
  • 94
    • 58949091514 scopus 로고    scopus 로고
    • note
    • For the preparation of sulfonamide 64, see Refs. 8 and 9. Sulfonamide 65 was prepared from (benzyloxy)-acetaldehyde, see Section 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.