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Volumn 71, Issue 9, 2006, Pages 3615-3618

Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of β-chloro-α-iodo- α,β-unsaturated esters

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTIONS; DICHLOROETHANE; UNSATURATED ESTERS;

EID: 33646261427     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060144h     Document Type: Article
Times cited : (102)

References (62)
  • 8
    • 0004246896 scopus 로고    scopus 로고
    • Krause, N., Ed.; Wiley-VCH: Weinheim, Germany
    • (a) Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002; p 224.
    • (2002) Modern Organocopper Chemistry , pp. 224
  • 22
    • 18744378312 scopus 로고    scopus 로고
    • and references therein
    • (e) Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765 and references therein.
    • (2005) J. Org. Chem. , vol.70 , pp. 3765
    • Zhou, C.1    Larock, R.C.2
  • 43
    • 33646269458 scopus 로고    scopus 로고
    • note
    • 3 immediately after the reaction facilitated subsequent purification by flash chromatography.
  • 47
    • 33646260638 scopus 로고    scopus 로고
    • note
    • This was confirmed by DEPT analysis of ester 1 and by subsequent NOE analysis of tetrasubstituted olefins 17-25.
  • 49
    • 0003441482 scopus 로고    scopus 로고
    • John Wiley & Sons: Ltd: Chichester, West Sussex, England; and references therein
    • General references: (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Ltd: Chichester, West Sussex, England, 2004; and references therein.
    • (2004) Palladium Reagents and Catalysts
    • Tsuji, J.1
  • 51
    • 4544239020 scopus 로고    scopus 로고
    • and references therein
    • Use of different vicinal olefinic halogens in cross-coupling reactions: Organ, M. G.; Ghasemi, H. Valente, C. Tetrahedron 2004, 60, 9453 and references therein.
    • (2004) Tetrahedron , vol.60 , pp. 9453
    • Organ, M.G.1    Ghasemi, H.2    Valente, C.3
  • 52
  • 54
    • 33646250612 scopus 로고    scopus 로고
    • note
    • 3CN, DMF, 1,4-dioxane, THF, and DMSO.
  • 55
    • 0034604562 scopus 로고    scopus 로고
    • Glaser-type products were prominent unless the reaction was carefully degassed prior to addition of the acetylenic component. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2632
    • Siemsen, P.1    Livingston, R.C.2    Diederich, F.3
  • 56
    • 33646263065 scopus 로고    scopus 로고
    • note
    • Multigram (3 g) scale reactions were performed successfully giving yields consistent with those shown.
  • 57
    • 33646262032 scopus 로고    scopus 로고
    • note
    • 11) with excess zinc reagent (ZnClPh-4-OMe) gave only ii and iii (1:1 ratio of E/Z isomers, no yield reported). In all cases, no trace of the α-coupled product was reported. Reference 10a. (Equation Presented)
  • 60
    • 33646256264 scopus 로고    scopus 로고
    • note
    • Reactions up to 500 mg scale were performed giving yields consistent with those shown.
  • 61
    • 33646250136 scopus 로고    scopus 로고
    • note
    • 13C, and GC-MS. This was prevented by storing the products frozen in benzene.
  • 62
    • 33646227863 scopus 로고    scopus 로고
    • note
    • A pure sample of 19 was separately reduced in order to verify the identity of the corresponding alcohol isomer 27.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.