Pyrrole syntheses based on titanium-catalyzed hydroamination of diynes

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2957-2960

  Ramanathan, Balasubramanian ^a   Keith, Adam J ^a   Armstrong, Douglas ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMINE; PYRROLE; TITANIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 4444383357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0489088     Document Type: Article

References (54)

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2. For reviews see: (a) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 2849-2866. (b) Jones, R. A., Ed. Pyrroles, Chemistry of Heterocyclic Compounds; Wiley: New York, 1990; Vol. 48.
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15. For examples, see: (a) Chalk, A. J. Tetrahedron Lett. 1972, 13, 3487-3490. (b) Chalk, A. J. Tetrahedron 1974, 30, 1387-1391. (c) Schulte, K. E.; Reisch, J.; Walker, H. Chem. Ber. 1965, 98, 98-103. Also, see pages 222-223 of Part 1 in ref 1b.
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22. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
23. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
24. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
25. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
26. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
27. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
28. For recent examples of pyrrole syntheses from imino alkynes, see: (a) Cossy, J.; Poitevin, C.; Sallé, L.; Pardo, D. G. Tetrahedron Lett. 1996, 37, 6709-6710. (b) Tarasova, O. A.; Nedolya, N. A.; Vvedensky, V. Y.; Brandsma, L.; Trofimov, B. A. Tetrahedron Lett. 1997, 38, 7241-7242. (c) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315-1317. (d) Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208. (e) Le, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992-4993. (f) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
29. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
30. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
31. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
32. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
33. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
34. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
35. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
36. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
37. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
38. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
39. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
40. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
41. Similar cyclizations have been explored in indole synthesis. For examples, see: (a) Fujiwara, J.; Fukutani, Y.; Sano, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 7177-7179. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (c) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690. (d) Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. H.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, V.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. J. Med. Chem. 1996, 39, 892-903. (e) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687-7690. (f) Larock, R. C.; Yam, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. (g) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162. (h) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (i) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (j) Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (k) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782. (l) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (m) van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717-1720.
42. Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075.
43. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 38, 2939-2947.
44. Trace of a product having a mass consistent with monohydroamination was observed, but it is not known if it was cyclized to the pyrrole.
45. For the synthesis of 1,4-diynes, see: Verkruijsse, H. D.; Hasselaar, M. Synthesis 1979, 292-293.
46. CAUTION: The starting materials for 1,4-diynes used in ref 19 are the propargyl tosylates. Explosions have resulted from purifying propargyl tosylate and its derivatives by vacuum distillation.
47. Yuguchi, M.; Tokuda, M.; Orito, K. J. Org. Chem. 2004, 69, 908-914.
48. The same symmetrical pyrroles, 3f and 3g, have been generated using Paal-Knorr synthesis and reported repeatedly in the literature. In typical examples, 3f and 3g were synthesized in 82 and 67% yields, respectively. Wothius, E.; Vander Jagt, D.; Mels, S.; De Boer, A. J. Org. Chem. 1965, 30, 190-193.
49. Davis, L. B.; Greenberg, S. G.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1981, 1909-1912.
50. Lucht, B. L.; Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 4354-4365.
51. Pyrrole 3h did not appear in our literature searches. However, a comparison can be made with 1,2,5-tribenzylpyrrole, which has been synthesized using Paal-Knorr in three steps from commercially available compounds in 42% yield overall. Wilcox, A. L.; Bao, Y. T.; Loeppky, R. N. Chem. Res. Toxicol. 1991, 4, 373-381. Our synthesis of 3h was accomplished in 61% overall yield in two steps.
52. Some 5-endo trig cyclizations are known. These often involve metal-mediated processes. For examples, see: (a) Trost, B. M.; Bonk, P. J. J. Am. Chem. Soc. 1985, 107, 1778-1781. (b) Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron Lett. 1985, 26, 4455-4458. Also see ref 16.
53. Some 5-endo trig cyclizations are known. These often involve metal-mediated processes. For examples, see: (a) Trost, B. M.; Bonk, P. J. J. Am. Chem. Soc. 1985, 107, 1778-1781. (b) Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron Lett. 1985, 26, 4455-4458. Also see ref 16.
54. To generate an α-vinyl pyrrole using Paal-Knorr synthesis would require reaction of an α,β-unsaturated ketone with an amine to generate the corresponding imine, a reaction that is often complicated by competing Michael addition. Hydroamination of the enyne can be used as an alternative procedure to α,β-unsaturated imines. Cao, C.; Li, Y.; Shi, Y.; Odom, A. L. Chem. Commun. In press.