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Volumn 9, Issue 20, 2007, Pages 4049-4052

Gold-catalyzed hydroamination/cycloisomerization reaction of 1,6-enynes

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; HYDROGEN;

EID: 35048818921     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7017483     Document Type: Article
Times cited : (80)

References (55)
  • 1
    • 35048895459 scopus 로고    scopus 로고
    • in press. For representative examples and seminal references, see: a
    • For representative examples and seminal references, see: (a) Michelet, V.; Toullec, P. Y.; Genet, J.-P. Angew. Chem., Int. Ed. 2007, 46, in press.
    • (2007) Angew. Chem., Int. Ed , vol.46
    • Michelet, V.1    Toullec, P.Y.2    Genet, J.-P.3
  • 14
    • 0000788623 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Müller, T. A.; Beller, M. Chem. Rev. 1998, 98, 675.
    • (1998) Chem. Rev , vol.98 , pp. 675
    • Müller, T.A.1    Beller, M.2
  • 28
    • 0037325107 scopus 로고    scopus 로고
    • Representative references: (a) Nevado, C.; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. P.; Méndez, M.; Rager, M.-N.; Genêt, J.-P.; Echavarren, A. M. Eur. J. Org. Chem. 2003, 706.
    • Representative references: (a) Nevado, C.; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. P.; Méndez, M.; Rager, M.-N.; Genêt, J.-P.; Echavarren, A. M. Eur. J. Org. Chem. 2003, 706.
  • 45
    • 35048888173 scopus 로고    scopus 로고
    • 6 (3-5 mol %, M = 343.6) in distilled THF or dioxane (2.5 M) was stirred under an argon atmosphere at room temperature for 3 min. The aminonucleophile (3 equiv) and then the enyne (1 equiv) were finally added. After completion of the reaction, the mixture was filtered through a short pad of silica gel (EtOAc) and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography.
    • 6 (3-5 mol %, M = 343.6) in distilled THF or dioxane (2.5 M) was stirred under an argon atmosphere at room temperature for 3 min. The aminonucleophile (3 equiv) and then the enyne (1 equiv) were finally added. After completion of the reaction, the mixture was filtered through a short pad of silica gel (EtOAc) and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography.
  • 47
    • 35048878409 scopus 로고    scopus 로고
    • TPPTS: tris(m-sulfonatophenyl)phosphane trisodium salt
    • (a) TPPTS: tris(m-sulfonatophenyl)phosphane trisodium salt.
  • 55
    • 35048871226 scopus 로고    scopus 로고
    • A mechanism relying on a concerted diastereoselective hydroamination/carbocyclization sequence leading directly to vinylaurate intermediate B cannot be ruled out
    • A mechanism relying on a concerted diastereoselective hydroamination/carbocyclization sequence leading directly to vinylaurate intermediate B cannot be ruled out.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.