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Volumn 75, Issue 23, 2010, Pages 8333-8336

Erratum: Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction (The Journal of Organic Chemistry (2010) 75 (8333) DOI: 10.1021/jo1019317));Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction

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Indexed keywords

CHEMICAL SHIFT;

EID: 78650260965     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102536d     Document Type: Erratum
Times cited : (25)

References (15)
  • 8
    • 78650265633 scopus 로고    scopus 로고
    • 3SiH was used for larger scale work
    • 3SiH was used for larger scale work.
  • 10
    • 78650270638 scopus 로고    scopus 로고
    • We were unable to contact Prof. Hostettmann (ref 2) to obtain an authentic sample for direct comparison
    • We were unable to contact Prof. Hostettmann (ref 2) to obtain an authentic sample for direct comparison.
  • 11
    • 78650277625 scopus 로고    scopus 로고
    • the isolation paper (ref 2), the configuration of the aromatic and carboxamide substituents on the core lactam are described as "cis", though they are depicted as trans (anti). We assumed this to be a typographical error. Our synthesis, which relies on methods to prepare the anticonfigured lactam (previuosly demonstrated by X-ray crystallography, see ref 5a), established that the configuration is anti. Attempts to crystallize 21, heliotropamide and several derivatives thereof were unsuccessful
    • In the isolation paper (ref 2), the configuration of the aromatic and carboxamide substituents on the core lactam are described as "cis", though they are depicted as trans (anti). We assumed this to be a typographical error. Our synthesis, which relies on methods to prepare the anticonfigured lactam (previuosly demonstrated by X-ray crystallography, see ref 5a), established that the configuration is anti. Attempts to crystallize 21, heliotropamide and several derivatives thereof were unsuccessful.
  • 12
    • 0000337713 scopus 로고
    • 1H NMR shifts of the vinylic proton in related alkylidene γ-lactams and lactones is generally 0.4-0.6 ppm higher upfield for the Z isomer when compared to the E isomer. See
    • 1H NMR shifts of the vinylic proton in related alkylidene γ-lactams and lactones is generally 0.4-0.6 ppm higher upfield for the Z isomer when compared to the E isomer. See: Lewis, F. D.; Oxman, J. D.; Gibson, L. L.; Hampsch, H. L.; Quillen, S. L. J. Am. Chem. Soc. 1986, 108, 3005-3015
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3005-3015
    • Lewis, F.D.1    Oxman, J.D.2    Gibson, L.L.3    Hampsch, H.L.4    Quillen, S.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.