Ruthenium-catalyzed reconstructive synthesis of cyclopentenones by unusual coupling of cyclobutenediones with alkenes involving carbon - carbon bond cleavage [17]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6319-6320

  Kondo, Teruyuki ^a   Nakamura, Ayako ^a   Okada, Takumi ^a   Suzuki, Nobuyoshi ^a   Wada, Kenji ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBON; CYCLOPENTENONE DERIVATIVE; RUTHENIUM;

CATALYSIS; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL REACTION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034608844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000238n     Document Type: Letter

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34. Coordination effect of an oxygen atom leading to C-H bond activation has been reported, (a) McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523. (b) Dauter, Z.; Mawby, R. J.; Reynolds, C. D.; Saunders, D. R. J. Chem. Soc., Dalton Trans. 1985, 1235. (c) Shu, A. Y. L.; Chen, W.; Heys, J. R. J. Organomet. Chem. 1996, 524, 87. For a catalytic reaction, see: (d) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
35. Coordination effect of an oxygen atom leading to C-H bond activation has been reported, (a) McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523. (b) Dauter, Z.; Mawby, R. J.; Reynolds, C. D.; Saunders, D. R. J. Chem. Soc., Dalton Trans. 1985, 1235. (c) Shu, A. Y. L.; Chen, W.; Heys, J. R. J. Organomet. Chem. 1996, 524, 87. For a catalytic reaction, see: (d) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
36. Coordination effect of an oxygen atom leading to C-H bond activation has been reported, (a) McGuiggan, M. F.; Pignolet, L. H. Inorg. Chem. 1982, 21, 2523. (b) Dauter, Z.; Mawby, R. J.; Reynolds, C. D.; Saunders, D. R. J. Chem. Soc., Dalton Trans. 1985, 1235. (c) Shu, A. Y. L.; Chen, W.; Heys, J. R. J. Organomet. Chem. 1996, 524, 87. For a catalytic reaction, see: (d) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
37. The Pauson-Khand reaction mediated or catalyzed by transition-metal complexes has been accepted as a powerful and convergent method for the construction of cyclopentenones; however, the use of alkyne substrates is essential for the reaction. For reviews, see: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, pp 703-739. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026 and references therein.
38. The Pauson-Khand reaction mediated or catalyzed by transition-metal complexes has been accepted as a powerful and convergent method for the construction of cyclopentenones; however, the use of alkyne substrates is essential for the reaction. For reviews, see: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, pp 703-739. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026 and references therein.