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Volumn 126, Issue 49, 2004, Pages 16066-16072

Ruthenium- and platinum-catalyzed sequential reactions: Selective synthesis of fused polycyclic compounds from propargylic alcohols and alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CATALYSIS; DERIVATIVES; MOLECULAR DYNAMICS; OLEFINS; PLATINUM; SYNTHESIS (CHEMICAL);

EID: 10344224589     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045532k     Document Type: Article
Times cited : (71)

References (59)
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • 0035861034 scopus 로고    scopus 로고
    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • Shimada, T.1    Mukaide, K.2    Shinohara, A.3    Han, J.W.4    Hayashi, T.5
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    • Tian, J.1    Yamagiwa, N.2    Matsunaga, S.3    Shibasaki, M.4
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • For recent examples, see: (a) Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620. (c) Christopher, J. L.; Bielawski, W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312. (d) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584. (e) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636. (f) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838. (g) Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693. (h) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (i) Klapars, A.; Parris, S.; Andersen, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
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    • note
    • 2RuCp*Cl] (1b) is commercially available from Wako Pure Chemical Industries (Japan) as met-DIRUX (methanethiolate-bridged diruthenium complex) (130-14581).
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    • note
    • 4m In this sequential reaction, however, the reaction conditions have to be changed on the way, and the successive addition of gold complex is necessary after the reaction of propargylic alcohol with allylsilane in the presence of rhenium complex. In contrast, it is noteworthy that, in our catalytic reaction system, both ruthenium and platinum catalysts sequentially promote each catalytic cycle in the same medium without changing the reaction conditions.


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