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Volumn 39, Issue 43, 2010, Pages 10401-10413

Studies in catalytic C-H amination involving nitrene C-H insertion

Author keywords

[No Author keywords available]

Indexed keywords

C-H INSERTION; COMPLEX MOLECULES; FUNCTIONALIZATIONS; GOOD YIELD; NITRENES; SITE SELECTIVE; STEREO-SELECTIVE;

EID: 78049330009     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/c0dt00283f     Document Type: Conference Paper
Times cited : (97)

References (92)
  • 1
    • 0004114335 scopus 로고
    • E. J. Corey and X.-M. Cheng, John Wiley & Sons, New York, 68
    • The Logic of Chemical Synthesis, E. J. Corey, and, X.-M. Cheng, John Wiley & Sons, New York, 1995, p. 68
    • (1995) The Logic of Chemical Synthesis
  • 3
    • 77349102962 scopus 로고    scopus 로고
    • Special issue "selective Functionalization of C-H Bonds"
    • For selected recent reviews, see: Special issue "Selective Functionalization of C-H Bonds", Chem. Rev., 2010, 110, pp. 575-1211
    • (2010) Chem. Rev. , vol.110 , pp. 575-1211
  • 73
    • 22244467723 scopus 로고    scopus 로고
    • For selected recent synthetic strategies towards allocolchicinoids, see: M. Leblanc K. Fagnou Org. Lett. 2005 7 2849
    • (2005) Org. Lett. , vol.7 , pp. 2849
    • Leblanc, M.1    Fagnou, K.2
  • 78
    • 78049342771 scopus 로고    scopus 로고
    • 2 and a sulfamate, led to the formation of the corresponding C-H aminated product with a low yield of 18%
    • 2 and a sulfamate, led to the formation of the corresponding C-H aminated product with a low yield of 18%.
  • 79
    • 78049329851 scopus 로고    scopus 로고
    • A test experiment starting from the homolog 1,4-diphenylbutane did not afford the corresponding C-H aminated product
    • A test experiment starting from the homolog 1,4-diphenylbutane did not afford the corresponding C-H aminated product.
  • 80
    • 78049330864 scopus 로고    scopus 로고
    • The observed ratio of 70% could have been attributed to the diastereoselective formation of regioisomers. However, this hypothesis was ruled out in the case of 6g by removing the o-bromo substituent under reductive conditions. This transformation was shown to give 6b as a mixture of isomers with a d.e. of 70%. Had we previously isolated regioisomers, this transformation would have led to a single product
    • The observed ratio of 70% could have been attributed to the diastereoselective formation of regioisomers. However, this hypothesis was ruled out in the case of 6g by removing the o-bromo substituent under reductive conditions. This transformation was shown to give 6b as a mixture of isomers with a d.e. of 70%. Had we previously isolated regioisomers, this transformation would have led to a single product.
  • 85
    • 0003674116 scopus 로고    scopus 로고
    • E. L. Eliel, S. H. Wilen and M. P. Doyle, Wiley Interscience, New York, 495 Should the kinetic resolution operate in the absence of the equilibrium between the enantiomeric iminoiodanes 16, no more than 55% of C-H aminated product will be isolated.
    • We are currently investigating whether the formation of diastereoisomers results from C-H amination of the two interconverting chair conformations of cis-decalin 14 which are not identical but enantiomers. See: Basic Organic Stereochemistry, E. L. Eliel, S. H. Wilen, and, M. P. Doyle, Wiley Interscience, New York, 2001, p. 495
    • (2001) Basic Organic Stereochemistry
  • 87
    • 78049331038 scopus 로고    scopus 로고
    • It should be pointed out that an unknown product resulting from a reaction between the metallanitrene and BHT was also isolated in the case of 2-methylbutane (yield in the 20-25% range). This could be responsible for the lower yield observed
    • It should be pointed out that an unknown product resulting from a reaction between the metallanitrene and BHT was also isolated in the case of 2-methylbutane (yield in the 20-25% range). This could be responsible for the lower yield observed
  • 92
    • 78049332185 scopus 로고    scopus 로고
    • 2 = 0.91)
    • 2 = 0.91).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.