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Volumn 51, Issue 21, 2010, Pages 2888-2891

Facile preparation of protected benzylic and heteroarylmethyl amines via room temperature Curtius rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AMINE; AZIDE; BENZILIC ACID; CHLOROFORM; METHANOL;

EID: 77951024881     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.101     Document Type: Article
Times cited : (18)

References (26)
  • 1
  • 2
    • 0001290085 scopus 로고
    • Degradation Reactions
    • Comprehensive Organic Synthesis - Selectivity. Trost B.M., and Fleming I. (Eds), Pergamon Press, New York
    • Shioiri T. Degradation Reactions. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis - Selectivity. Strategy & Efficiency in Modern Organic Chemistry Vols. 6, 4.4 (1991), Pergamon Press, New York 795-828
    • (1991) Strategy & Efficiency in Modern Organic Chemistry , pp. 795-828
    • Shioiri, T.1
  • 6
    • 4344670098 scopus 로고    scopus 로고
    • For an example of a benzylic substrate successfully used with DPPA see:
    • For an example of a benzylic substrate successfully used with DPPA see:. Spino C., Tremblay M.-C., and Gobdout C. Org. Lett. 6 (2004) 2801-2804
    • (2004) Org. Lett. , vol.6 , pp. 2801-2804
    • Spino, C.1    Tremblay, M.-C.2    Gobdout, C.3
  • 8
    • 77951025750 scopus 로고    scopus 로고
    • note
    • This byproduct was observed by LC-MS.
  • 15
    • 77951023783 scopus 로고    scopus 로고
    • note
    • 3N, and MeOH or t-BuOH), which led to numerous side products instead of rearrangement product 10a.
  • 16
    • 77951023448 scopus 로고    scopus 로고
    • note
    • Attempts to increase the rate of conversion to 10a by addition of catalytic HCl, and other more acidic alchohol solvents such as hexafluoroisopropanol and trifluoroethanol led in all cases to ester byproducts in addition to product 10a.
  • 23
    • 0037151592 scopus 로고    scopus 로고
    • 3 could also be responsible, see:
    • 3 could also be responsible, see:. Huang Y., and Rawal V.H. J. Am. Chem. Soc. 124 (2002) 9662-9663
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9662-9663
    • Huang, Y.1    Rawal, V.H.2
  • 24
    • 77951023808 scopus 로고    scopus 로고
    • note
    • Note that the majority of commercially purchased chloroform is stabilized with added ethanol, even if unspecified. Ethanol can compete with other alcohol nucleophiles to trap the isocyanate intermediate. We recommend using anhydrous chloroform stabilized with amylenes to avoid this complication.
  • 26
    • 77951023348 scopus 로고
    • Although acyl azides are a widely used intermediate in organic synthesis, the authors caution that low molecular weight acyl azides can be potentially explosive if evaporated to dryness. See: On larger scale, the authors recommend partial concentration of the acyl azide intermediate, followed by introduction of MeOH
    • Although acyl azides are a widely used intermediate in organic synthesis, the authors caution that low molecular weight acyl azides can be potentially explosive if evaporated to dryness. See:. Overman L.E., Jessup P.J., Petty C.B., and Roos J. Org. Synth. 59 (1980) 1 On larger scale, the authors recommend partial concentration of the acyl azide intermediate, followed by introduction of MeOH
    • (1980) Org. Synth. , vol.59 , pp. 1
    • Overman, L.E.1    Jessup, P.J.2    Petty, C.B.3    Roos, J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.