Nitrogenous educts through oxidative amidation of phenols: The bimolecular reaction

Organic Letters

Volumn 7, Issue 2, 2005, Pages 175-177

  Canesi, Sylvain ^a   Bouchu, Denis ^a   Ciufolini, Marco A ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; ACETONITRILE; IODOBENZENE; PHENOL DERIVATIVE; PROPRANOLOL DERIVATIVE;

AMIDATION; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 13444261090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048094v     Document Type: Article

References (31)

1. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
2. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
3. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
4. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
5. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
6. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
7. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
8. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
9. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
10. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
11. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
12. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
13. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
14. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
15. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
16. Leading references and noteworthy examples of reactions of this type: (a) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett 2003, 1352. (d) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (e) Narasaka, K. Pure App. Chem. 2002, 74, 143. (f) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. (g) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268. (h) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149. (j) Prata, J. V.; Clemente, D.-T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513. (k) Telma, D.; Clemente, V.; Lobo, A. M.; Prabhakar, S.; Marcelo-Curto, M. J. Tetrahedron Lett. 1994, 35, 2043. (l) Hartshorn, M. P.; Judd, M. C.; Vannoort, R. W.; Wright, G. J. Aust. J. Chem. 1989, 42, 689. (m) Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Heterocvcles 1983, 20, 1481. (n) Hashimoto, Y.; Ohta, T.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1979, 20, 1611. (o) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577. (p) Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653.
17. (a) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667.
18. (b) Braun, N. A.; Bray, J.; Ousmer, M.; Peters, K.; Peters, E.-M., Bouchu, D.; Ciufolini, M. A. J. Org Chem. 2000, 65, 4397.
19. (c) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7534.
20. (a) Canesi, S.; Belmont, P.; Bouchu, D.; Rousset, L.; Ciufolini, M. A. Tetrahedron Lett. 2002, 43, 5193
21. (b) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2004, 43, 4336; Angew. Chem. 2004, 116, 4436.
22. (b) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2004, 43, 4336; Angew. Chem. 2004, 116, 4436.
23. Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593.
24. Mizutani, H.; Takayama, J.; Soeda, Y.; Honda, T. Tetrahedron Lett. 2002, 43, 2411.
25. This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. (a) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857. (b) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
26. This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. (a) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857. (b) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
27. This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. (a) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857. (b) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
28. These experiments were inspired by the success of our sulfonamide-based methodology (ref 3).
29. Drutu, I.; Njardarson, J. T.; Wood, J. L. Org. Lett. 2002, 4, 493.
30. A similar reaction forms the basis of an interesting synthesis of aculeatins A and B. Cf. Wong, Y. S. J. Chem. Soc., Chem. Commun. 2002, 686.
31. 2) provided the pure product.