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Volumn 4, Issue 15, 2002, Pages 2465-2468

Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; ETHYLENE DERIVATIVE; INDACRINONE; INDAN DERIVATIVE; KETENE; KETONE; TRIMETHYLSILYL DERIVATIVE;

EID: 0041382928     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026014m     Document Type: Article
Times cited : (40)

References (35)
  • 2
    • 0003828015 scopus 로고
    • Wiley: New York
    • Reviews: (a) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
    • (1995) Ketenes
    • Tidwell, T.T.1
  • 12
    • 0013557296 scopus 로고
    • Scattered reports have appeared previously in which indanone derivatives were observed in the reaction of diazo compounds with diarylketenes. See: (a) Kende, A. S. Chem. Ind. (London) 1956, 1053.
    • (1956) Chem. Ind. (London) , pp. 1053
    • Kende, A.S.1
  • 16
    • 0000475010 scopus 로고
    • For generation of silylketenes by photo-Wolff rearrangement, see refs 4-6 and: (a) Maas, G.; Brückmann, R. J. Org. Chem. 1985, 50, 2801.
    • (1985) J. Org. Chem. , vol.50 , pp. 2801
    • Maas, G.1    Brückmann, R.2
  • 18
    • 0033532916 scopus 로고    scopus 로고
    • Wolff rearrangement of α-silyl-α-diazo ketones can also be effected by heating in the presence of catalytic rhodium(II) octanoate; see: Marsden, S. P.; Pang, W.-K. J. Chem. Soc., Chem. Commun. 1999, 1199.
    • (1999) J. Chem. Soc., Chem. Commun. , pp. 1199
    • Marsden, S.P.1    Pang, W.-K.2
  • 19
    • 84872270191 scopus 로고    scopus 로고
    • note
    • 9a,b
  • 22
    • 84872275530 scopus 로고    scopus 로고
    • note
    • 3.
  • 25
    • 0001992172 scopus 로고
    • Paquette, L. A., Ed.; Wiley: New York
    • Pentadienyl cation electrocyclic ring closures are involved in the mechanism of the Nazarov cyclization. For reviews, see: (a) Habermas, K. L.; Denmark, S. E. In Organic Reactions: Paquette, L. A., Ed.; Wiley: New York, 1994; Vol. 45, pp 1-158.
    • (1994) Organic Reactions , vol.45 , pp. 1-158
    • Habermas, K.L.1    Denmark, S.E.2
  • 26
    • 0000646877 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon; Oxford
    • (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon; Oxford, 1991; Vol. 5, p 751.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751
    • Denmark, S.E.1
  • 27
    • 84872278528 scopus 로고    scopus 로고
    • note
    • Alternatively, cyclization of intermediate 15 could produce the five-membered ring product 18 directly, although the planar structure of the dienolate system may not allow it to achieve an arrangement in which the π electrons are suitably situated for direct backside displacement of the leaving group.
  • 34
    • 84872275338 scopus 로고    scopus 로고
    • note
    • Stereochemistry of 20 assigned as shown on the basis of NOE experiments and analysis of proton NMR coupling constant data; see Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.