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Volumn 125, Issue 20, 2003, Pages 6060-6061

Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; CARBON; METAL COMPLEX; RUTHENIUM;

EID: 0038366633     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035106j     Document Type: Article
Times cited : (95)

References (28)
  • 12
    • 0034659735 scopus 로고    scopus 로고
    • Some allenylidene ruthenium complexes worked as precatalysts for the ring-closing metathesis: (a) Fürstner, A.; Liebel, M.; Lehmann, C. W.; Picquet, M.; Kunz, R.; Bruneau, C.; Touchard, D.; Dixneuf, P. H. Chem.Eur. J. 2000, 6, 1847. (b) Harlow, K. J.; Hill, A. F.; Wilton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. (c) Jafarpour, L.; Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 3760.
    • (2000) Chem.Eur. J. , vol.6 , pp. 1847
    • Fürstner, A.1    Liebel, M.2    Lehmann, C.W.3    Picquet, M.4    Kunz, R.5    Bruneau, C.6    Touchard, D.7    Dixneuf, P.H.8
  • 13
    • 33750595439 scopus 로고    scopus 로고
    • Some allenylidene ruthenium complexes worked as precatalysts for the ring-closing metathesis: (a) Fürstner, A.; Liebel, M.; Lehmann, C. W.; Picquet, M.; Kunz, R.; Bruneau, C.; Touchard, D.; Dixneuf, P. H. Chem.Eur. J. 2000, 6, 1847. (b) Harlow, K. J.; Hill, A. F.; Wilton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. (c) Jafarpour, L.; Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 3760.
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 285
    • Harlow, K.J.1    Hill, A.F.2    Wilton-Ely, J.D.E.T.3
  • 14
    • 0001451058 scopus 로고    scopus 로고
    • Some allenylidene ruthenium complexes worked as precatalysts for the ring-closing metathesis: (a) Fürstner, A.; Liebel, M.; Lehmann, C. W.; Picquet, M.; Kunz, R.; Bruneau, C.; Touchard, D.; Dixneuf, P. H. Chem.Eur. J. 2000, 6, 1847. (b) Harlow, K. J.; Hill, A. F.; Wilton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. (c) Jafarpour, L.; Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 3760.
    • (1999) Organometallics , vol.18 , pp. 3760
    • Jafarpour, L.1    Huang, J.2    Stevens, E.D.3    Nolan, S.P.4
  • 15
    • 0032901722 scopus 로고    scopus 로고
    • For recent examples of ruthenium-catalyzed reactions with propargylic alcohols, see: (a) Dérien, S.; Ropartz, L.; Paih, J. L.; Dixneuf, P. H. J. Org. Chem. 1999, 64, 3524. (b) Paih, J. L.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem. Int. Ed. 2001, 40, 2912. (c) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862. (d) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531.
    • (1999) J. Org. Chem. , vol.64 , pp. 3524
    • Dérien, S.1    Ropartz, L.2    Paih, J.L.3    Dixneuf, P.H.4
  • 16
    • 0035800388 scopus 로고    scopus 로고
    • For recent examples of ruthenium-catalyzed reactions with propargylic alcohols, see: (a) Dérien, S.; Ropartz, L.; Paih, J. L.; Dixneuf, P. H. J. Org. Chem. 1999, 64, 3524. (b) Paih, J. L.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem. Int. Ed. 2001, 40, 2912. (c) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862. (d) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2912
    • Paih, J.L.1    Dérien, S.2    Bruneau, C.3    Demerseman, B.4    Toupet, L.5    Dixneuf, P.H.6
  • 17
    • 0035850537 scopus 로고    scopus 로고
    • For recent examples of ruthenium-catalyzed reactions with propargylic alcohols, see: (a) Dérien, S.; Ropartz, L.; Paih, J. L.; Dixneuf, P. H. J. Org. Chem. 1999, 64, 3524. (b) Paih, J. L.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem. Int. Ed. 2001, 40, 2912. (c) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862. (d) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8862
    • Trost, B.M.1    Rudd, M.T.2
  • 18
    • 0037078485 scopus 로고    scopus 로고
    • For recent examples of ruthenium-catalyzed reactions with propargylic alcohols, see: (a) Dérien, S.; Ropartz, L.; Paih, J. L.; Dixneuf, P. H. J. Org. Chem. 1999, 64, 3524. (b) Paih, J. L.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem. Int. Ed. 2001, 40, 2912. (c) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862. (d) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7531
    • Suzuki, T.1    Tokunaga, M.2    Wakatsuki, Y.3
  • 23
    • 0034683054 scopus 로고    scopus 로고
    • and references therein
    • The thiolate-bridged diruthenium complexes (1a-1d) have been found to provide unique bimetallic reaction sites for activation and transformation of various terminal alkynes, see: Nishibayashi, Y.; Yamanashi, M.; Wakiji, I.; Hidai, M. Angew. Chem., Int. Ed. 2000, 39, 2909 and references therein.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2909
    • Nishibayashi, Y.1    Yamanashi, M.2    Wakiji, I.3    Hidai, M.4
  • 25
    • 0038368378 scopus 로고    scopus 로고
    • note
    • NOE experiments of major products of 5 were performed to determine their stereochemistry. See the Supporting Information for experimental details.
  • 27
    • 33845281351 scopus 로고
    • and references therein
    • (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207 and references therein.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 207
    • Nicholas, K.M.1
  • 28
    • 0346265937 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, Chapter 71
    • (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II: Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995: Vol. 12, Chapter 7.1.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Caffyn, A.J.M.1    Nicholas, K.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.