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Volumn 48, Issue 33, 2007, Pages 5887-5889

Catalytic annulation of 1-substituted-3-en-1-yn-5-als with cycloalkanones using acid-base dual catalysts

Author keywords

[No Author keywords available]

Indexed keywords

1 TETRALONE DERIVATIVE; ACID; BASE; BENZENE; CYCLOALKANONE; INDANONE DERIVATIVE; RUTHENIUM;

EID: 34447536312     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.045     Document Type: Article
Times cited : (9)

References (24)
  • 1
    • 0027999819 scopus 로고
    • For review, see:
    • For review, see:. Hall N. Science 266 (1994) 32
    • (1994) Science , vol.266 , pp. 32
    • Hall, N.1
  • 10
    • 0029860625 scopus 로고    scopus 로고
    • For catalytic aromatization of 3,5-dien-1-ynes via metal-vinylidene intermediates, see selected examples:
    • For catalytic aromatization of 3,5-dien-1-ynes via metal-vinylidene intermediates, see selected examples:. Merlic C.A., and Pauly M.E. J. Am. Chem. Soc. 118 (1996) 11319
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11319
    • Merlic, C.A.1    Pauly, M.E.2
  • 15
    • 4744342870 scopus 로고    scopus 로고
    • For catalytic aromatization 3,5-dien-1-ynes via metal-π-alkyne intermediates, see: and references cited therein
    • For catalytic aromatization 3,5-dien-1-ynes via metal-π-alkyne intermediates, see:. Mamane V., Hannen P., and Fürstner A. Chem. Eur. J. 10 (2004) 4556 and references cited therein
    • (2004) Chem. Eur. J. , vol.10 , pp. 4556
    • Mamane, V.1    Hannen, P.2    Fürstner, A.3
  • 19
    • 9444297050 scopus 로고    scopus 로고
    • For the catalytic Mukaiyama aldol-dehydration sequence, see selected examples:
    • For the catalytic Mukaiyama aldol-dehydration sequence, see selected examples:. Yanagisawa A., Coudu R., and Arai T. Org. Lett. 6 (2004) 4281
    • (2004) Org. Lett. , vol.6 , pp. 4281
    • Yanagisawa, A.1    Coudu, R.2    Arai, T.3
  • 21
    • 34447561300 scopus 로고    scopus 로고
    • note
    • 20O: 276.1514; found, 276.1519.
  • 22
    • 34447557400 scopus 로고    scopus 로고
    • note
    • Formation of an enolate requires a base, whereas an acid favors dehydration of the aldol products. For the acid/base combined systems for aldol condensation and dehydration sequence, see: Refs. 2a,b and references cited therein.
  • 23
    • 34447534903 scopus 로고    scopus 로고
    • note
    • The Ru/DBU mixture is not suitable for 1-silyl-3-en-1-yn-5-al 1 in this tandem catalysis due to the occurrence of desilylation, which gave desilylated benzene 3 in 23% yield.
  • 24
    • 34447575389 scopus 로고    scopus 로고
    • note
    • The role of this dual catalyst in this tandem catalysis is shown by the data in Scheme 2 (entries 5 and 6) and Table 2 (entries 5-7), which reveal that this catalyst combination not only enhanced aldol condensation, but also the subsequent aromatization reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.