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Volumn 10, Issue 5, 2008, Pages 1025-1028

Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis

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EID: 45549094465     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800092p     Document Type: Article
Times cited : (144)

References (41)
  • 11
  • 15
    • 36849037731 scopus 로고    scopus 로고
    • For a related Hg(II)-induced carbocyclization, see: Boaventura, M. A.; Drouin, J. Synth. Commun. 1987, 17, 975.
    • For a related Hg(II)-induced carbocyclization, see: Boaventura, M. A.; Drouin, J. Synth. Commun. 1987, 17, 975.
  • 25
    • 32844457119 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) List, B. Chem. Commun. 2006, 819.
    • (2006) Chem. Commun , pp. 819
    • List, B.1
  • 30
    • 33646573235 scopus 로고    scopus 로고
    • For the use of catalytically generated enamines in transition metal-catalyzed reactions, see: a
    • For the use of catalytically generated enamines in transition metal-catalyzed reactions, see: (a) Ibrahem, I.; Cordova, A. Angew. Chem., Int. Ed. 2006, 45, 1952.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1952
    • Ibrahem, I.1    Cordova, A.2
  • 36
    • 58149187082 scopus 로고    scopus 로고
    • We assume that initially formed 2a isomerizes directly into the more stable conjugated compound 3a in the presence of HN(i-Pr) 2 at 70 °C
    • 2 at 70 °C.
  • 37
    • 58149200142 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixtures.
    • 1H NMR analysis of the crude reaction mixtures.
  • 38
    • 58149182847 scopus 로고    scopus 로고
    • General Procedure. Synthesis of 2h (Table 2, entry 7, A solution of 1h (100 mg, 0.42 mmol) and (c-C6H 11)(i-Pr)NH (20 mol, 12 mg) in CDC13 (0.4 mL) was added to, Ph3PAu)3O]BF4 (7.5 mol, 45 mg, and the reaction vial was sealed, protected from light, and stirred at 70 °C for 18 h (until 1H NMR analysis of the reaction mixture indicated complete conversion, The mixture was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (pentanes/EtOAc, 95/5) gave 2h as a colorless oil (71 mg, 0.30 mmol, 71, R f0.48 (pentanes/EtOAc, 90/10, 1H NMR (360 MHz, CDC13) δ 1.26 (s, 3H, 2.23 (d, J, 14.0 Hz, 1 H, 2.92-3.07 (m, 3 H, 3.73 (s, 3 H, 3.74 (s, 3 H, 4.95 (app. t, J, 2.2 Hz, 1 H, 5.22 (app. t, J, 1.9 Hz, 1 H, 9.29 (s, 1 H, 13C NMR 90.6 MHz, CDC
    • 3O)].
  • 40
    • 58149179152 scopus 로고    scopus 로고
    • This ring system has not been previously described in the literature
    • This ring system has not been previously described in the literature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.