Gold- and silver-catalyzed highly regioselective addition of active methylenes to dienes, triene, and cyclic enol ethers

Organic Letters

Volumn 7, Issue 4, 2005, Pages 673-675

  Nguyen, Rene Viet ^a   Yao, Xiao Quan ^a   Bohle, D Scott ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CARBENE; CARBON; ETHER; GOLD; SILVER; TRIENTINE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; STEREOCHEMISTRY;

EID: 14844341867     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047543o     Document Type: Article

References (39)

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10. During the preparation of this manuscript, Hartwig and co-workers reported a similar reaction of dienes with palladium. See: Leitner, A.; Larsen, J.; Steffens, C.; Hartwig, J. F. J. Org. Chem. 2004, 69, 7552.
11. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
12. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
13. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
14. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
15. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
16. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
17. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
18. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
19. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
20. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
21. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
22. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
23. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
24. For other examples of gold-catalyzed reactions, see: Ito, Y.; Sawamura, T.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563. Deetlefs, M.; Raubenheimer, H. G.; Esterhuygen, M. W. Catal. Today 2002, 72, 29. Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964. Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 34, 1247. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarre, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239. Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
25. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
26. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
27. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
28. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
29. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
30. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
31. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
32. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
33. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
34. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
35. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
36. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
37. For other examples of silver-catalyzed reactions, see: Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475. Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088. Hayashi, T.; Uozumi, Y.; Yamazaki, A.; Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron. Lett. 1991, 32, 2799. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038. Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377. Xu, C.; Negishi, E. I. Tetrahedron Lett. 1999, 40, 431. Wipf, P.; Methot, J. L. Org. Lett. 1999, 1, 1253. Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. Burgess, K. Chem. Ind. 1999, 18, 716. Bianchini, C.; Glendenning, L. Chemtracts 1997, 10, 339.
38. Previously, the addition of activated methylene to dihydrofuran and pyrans catalyzed by trifluoroacetic acid has been reported; see: Bihovsky, R.; Kumar, M. U.; Ding, S.; Goyal, A. J. Org. Chem. 1989, 54, 4291.
39. We thank the reviewers tor their suggestions regarding this mechanism.