Pt(II) or Ag(I) salt catalyzed cycloisomerizations and tandem cycloadditions forming functionalized azacyclic arrays

Organic Letters

Volumn 6, Issue 26, 2004, Pages 5023-5026

  Harrison, Tyler J ^a   Dake, Gregory R ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; DECALIN DERIVATIVE; FUNCTIONAL GROUP; PLATINUM; SILVER; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; ELECTRON; ISOMERIZATION; STEREOCHEMISTRY;

ALKYNES; AZA COMPOUNDS; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PLATINUM; SILVER; STEREOISOMERISM;

EID: 12344293484     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047696b     Document Type: Article

References (44)

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3. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
4. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
5. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
6. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
7. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
8. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
9. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
10. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
11. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
12. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
13. Representative synthetic studies. Nakadomarin A: (a) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020-2023. (b) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947-950. (c) Fürstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem: A Eur. J. 2001, 7, 4811-4820. Tabersonine: (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628-4641. (e) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519-1522. (f) Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y. L.; Wang, T. S. J. Org. Chem. 1998, 63, 2172-2183. Streptazolin: (g) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327-4329. (h) Huang, S. L.; Comins, D. L. Chem. Commun. 2000, 569-570. (i) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059. (j) Kozikowski, A. P.; Park, P. J. Org. Chem. 1990, 55, 4668-4682. (k) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115-6118.
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25. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
26. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
27. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
28. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
29. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
30. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
31. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
32. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
33. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
34. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
35. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
36. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
37. For examples, see: (a) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520. (d) Fürstner, A.; Stelzer, F., Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709. (f) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385-388. (g) Kisanga, P.; Goj, L. A.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 635-637. (h) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 62, 5197-5201. (i) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766. (j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701. (k) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409. (l) Mamane, V.; Gress, T.; Krause, H. Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655. For reviews, see: (m) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425. (n) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627-2635.
38. The substrates used in this study are readily available in five to seven steps from N-p-toluenesulfonyl-2-piperidone, as adapted from the method of Shono: Shono, T.; Terauchi, J.; Ohki, Y.; Matsumura, Y. Tetrahedron Lett. 1990, 31, 6385-6286.
39. 3.
40. (a) Li, J. J.; Li, W.; Sharp, P. R. Inorg. Chem. 1996, 35, 604-613.
41. (b) Gavagnin, R.; Cataldo, M.; Pinna, F.; Strukul, G. Organometallics 1998, 17, 661-667.
42. These experiments are presented in the Supporting Information.
43. For some reviews of "tandem" or "domino" reactions, see: (a) Neushutz, K.; Velker, J.; Neier, R. Synthesis 1998, 227-255. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
44. For some reviews of "tandem" or "domino" reactions, see: (a) Neushutz, K.; Velker, J.; Neier, R. Synthesis 1998, 227-255. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.