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Volumn 7, Issue 14, 2005, Pages 3081-3084

Copper-catalyzed stereospecific N-allenylations of amides. Syntheses of optically enriched chiral allenamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COPPER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

EID: 22244434207     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051094q     Document Type: Article
Times cited : (68)

References (70)
  • 1
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    • For a recent review on copper-mediated C-N and C-O bond formation, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5400
    • Ley, S.V.1    Thomas, A.W.2
  • 2
  • 3
    • 0032541260 scopus 로고    scopus 로고
    • For reviews on the related palladium-catalyzed N-arylations of amines and amides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046
    • Hartwig, J.F.1
  • 6
  • 9
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    • and references therein
    • For an earlier account, see: Yamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86 and references therein.
    • (1983) Can. J. Chem. , vol.61 , pp. 86
    • Yamamoto, T.1    Kurata, Y.2
  • 10
    • 2442544350 scopus 로고    scopus 로고
    • For some recent references of copper-catalyzed aminations and amidations: (a) Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5680
    • Berman, A.M.1    Johnson, J.S.2
  • 61
    • 32744458893 scopus 로고    scopus 로고
    • note
    • See Supporting Information for experimental procedures and characterizations of new compounds.
  • 62
    • 32744455455 scopus 로고    scopus 로고
    • note
    • Trost reported some successful examples of couplings with allenyl bromide. See ref 12.
  • 63
    • 4544320494 scopus 로고    scopus 로고
    • Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim
    • For reviews on allenes, see: (a) Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2004; Vols. 1 and 2.
    • (2004) Modern Allene Chemistry , vol.1-2
    • Krause, N.1    Hashmi, A.S.K.2
  • 64
    • 0002266484 scopus 로고
    • Heterosubstituierte Allene and Polyallene
    • Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
    • (b) Saalfrank, R. W.; Lurz, C. J. Heterosubstituierte Allene and Polyallene. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3093-3102.
    • (1993) Methoden der Organischen Chemie (Houben-Weyl) , pp. 3093-3102
    • Saalfrank, R.W.1    Lurz, C.J.2
  • 70
    • 32744477177 scopus 로고    scopus 로고
    • note
    • These amides were chosen because we were able to resolve their respective enantiomeric allenamides distinctly on using HPLC on a Chiralcel-OD chiral column with a UV detector [see Supporting Information].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.