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Volumn 70, Issue 8, 2005, Pages 3140-3147

Oxidative formation of thiolesters in a model system of the pyruvate dehydrogenase complex

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSTS; CORRELATION METHODS; ELECTRONIC STRUCTURE; ENZYMES; OXIDATION; REACTION KINETICS;

EID: 17444420326     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047737h     Document Type: Article
Times cited : (33)

References (42)
  • 20
    • 3543074145 scopus 로고    scopus 로고
    • The analogous conversion of α-haloaldehydes and α,β-unsaturated aldehydes into acylating agents catalyzed by nucleophilic carbenes has been reported: (a) Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518. (b) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205. (c) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9518
    • Reynolds, N.T.1    De Alaniz, J.R.2    Rovis, T.3
  • 21
    • 10044249952 scopus 로고    scopus 로고
    • The analogous conversion of α-haloaldehydes and α,β-unsaturated aldehydes into acylating agents catalyzed by nucleophilic carbenes has been reported: (a) Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518. (b) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205. (c) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6205
    • Burstein, C.1    Glorius, F.2
  • 22
    • 7744232978 scopus 로고    scopus 로고
    • The analogous conversion of α-haloaldehydes and α,β-unsaturated aldehydes into acylating agents catalyzed by nucleophilic carbenes has been reported: (a) Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518. (b) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205. (c) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14370
    • Sohn, S.S.1    Rosen, E.L.2    Bode, J.W.3
  • 25
    • 17444382790 scopus 로고    scopus 로고
    • note
    • We could not identify what acted as an oxidizing agent in this reaction, although it appeared that contaminating molecular oxygen was at least partly responsible for the formation of these oxidation products.
  • 26
    • 17444366260 scopus 로고    scopus 로고
    • note
    • When 3-phenylpropanal was treated under the reaction conditions described in the text, the corresponding hydrazide was predominately obtained (55%), along with small amounts of the thiolester (6%). Thus, some modifications of the reaction conditions are required to employ this method for the synthesis of thiolesters derived from aliphatic aldehydes, which are ongoing in our laboratory.
  • 30
    • 0004053307 scopus 로고
    • Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York
    • Exner, O. In Correlation Analysis in Chemistry; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978.
    • (1978) Correlation Analysis in Chemistry
    • Exner, O.1
  • 39
    • 17444401444 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the reaction mixture, were produced in yields comparable to those in the azobenzene oxidation.


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