Ru(II)-catalyzed cycloadditions of 1,6-heptadiynes with alkenes: New synthetic potential of ruthenacyclopentatrienes as biscarbenoids in tandem cyclopropanation of bicycloalkenes and heteroatom-assisted cyclocotrimerization of 1,6-heptadiynes with heterocyclic alkenes

Journal of the American Chemical Society

Volumn 122, Issue 18, 2000, Pages 4310-4319

  Yamamoto, Yoshihiko ^a   Kitahara, Hideaki ^a   Ogawa, Ryuji ^a   Kawaguchi, Hiroyuki ^a   Tatsumi, Kazuyuki ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICYCLOPROPYLCYCLOPENTENE; ALKENE DERIVATIVE; CARBENOID; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; NORBORNENE DERIVATIVE; RUTHENACYCLOPENTATRIENE; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE; X RAY ANALYSIS;

EID: 0034630934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9942890     Document Type: Article

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85. Ruthenacyclopentene formations were proposed to be a key step in the Ru-catalyzed reactions of alkynes and alkenes or of enynes, see: (a) Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831. (b) Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985. (c) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. (e) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. (f) Trost, B. M.; Roth, G. J. Org. Lett. 1999, 1, 67. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187 and also see refs 17 and 29b-d.
86. Ruthenacyclopentene formations were proposed to be a key step in the Ru-catalyzed reactions of alkynes and alkenes or of enynes, see: (a) Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831. (b) Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985. Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. (e) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. (f) Trost, B. M.; Roth, G. J. Org. Lett. 1999, 1, 67. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187 and also see refs 17 and 29b-d.
87. Ruthenacyclopentene formations were proposed to be a key step in the Ru-catalyzed reactions of alkynes and alkenes or of enynes, see: (a) Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831. (b) Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985. (c) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. (e) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. (f) Trost, B. M.; Roth, G. J. Org. Lett. 1999, 1, 67. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187 and also see refs 17 and 29b-d.
88. Ruthenacyclopentene formations were proposed to be a key step in the Ru-catalyzed reactions of alkynes and alkenes or of enynes, see: (a) Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831. (b) Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985. (c) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. (e) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. (f) Trost, B. M.; Roth, G. J. Org. Lett. 1999, 1, 67. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187 and also see refs 17 and 29b-d.
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