Second-chance rearrangement route to novel 5(6)-syn,anti-difunctional 2-azabicyclo[2.1.1]hexanes

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2739-2741

  Krow, Grant R ^a   Lin, Guoliang ^a   Yu, Fang ^a   Sonnet, Philip E ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BICYCLO COMPOUND; HEXANE; IODIDE; MERCURY; SILVER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0141855033     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0349662     Document Type: Article

References (32)

1. For a leading reference to synthetic approaches to 2-azabicyclo[2.1.1]-hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259 and refs 5-7 therein. For additional nucleophilic ring closure approaches, see: (b) Rammeloo, T.; Stevens, C. V. J. Chem. Soc., Chem. Commun. 2002, 250. (c) Rammeloo, T.; Stevens, C. V.; De Kimpe, N. J. Org. Chem. 2002, 67, 6509. (d) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187. (e) Rammeloo, T.; Stevens, C. V. New J. Chem. 2003, 27, 668. For additional photochemical approaches to 2-azabicyclo[2.1.1]hexanes, see: (f) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. (h) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165.
2. For a leading reference to synthetic approaches to 2-azabicyclo[2.1.1]-hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259 and refs 5-7 therein. For additional nucleophilic ring closure approaches, see: (b) Rammeloo, T.; Stevens, C. V. J. Chem. Soc., Chem. Commun. 2002, 250. (c) Rammeloo, T.; Stevens, C. V.; De Kimpe, N. J. Org. Chem. 2002, 67, 6509. (d) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187. (e) Rammeloo, T.; Stevens, C. V. New J. Chem. 2003, 27, 668. For additional photochemical approaches to 2-azabicyclo[2.1.1]hexanes, see: (f) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. (h) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165.
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4. For a leading reference to synthetic approaches to 2-azabicyclo[2.1.1]-hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259 and refs 5-7 therein. For additional nucleophilic ring closure approaches, see: (b) Rammeloo, T.; Stevens, C. V. J. Chem. Soc., Chem. Commun. 2002, 250. (c) Rammeloo, T.; Stevens, C. V.; De Kimpe, N. J. Org. Chem. 2002, 67, 6509. (d) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187. (e) Rammeloo, T.; Stevens, C. V. New J. Chem. 2003, 27, 668. For additional photochemical approaches to 2-azabicyclo[2.1.1]hexanes, see: (f) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. (h) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165.
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6. For a leading reference to synthetic approaches to 2-azabicyclo[2.1.1]-hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259 and refs 5-7 therein. For additional nucleophilic ring closure approaches, see: (b) Rammeloo, T.; Stevens, C. V. J. Chem. Soc., Chem. Commun. 2002, 250. (c) Rammeloo, T.; Stevens, C. V.; De Kimpe, N. J. Org. Chem. 2002, 67, 6509. (d) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187. (e) Rammeloo, T.; Stevens, C. V. New J. Chem. 2003, 27, 668. For additional photochemical approaches to 2-azabicyclo[2.1.1]hexanes, see: (f) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. (h) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165.
7. For a leading reference to synthetic approaches to 2-azabicyclo[2.1.1]-hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259 and refs 5-7 therein. For additional nucleophilic ring closure approaches, see: (b) Rammeloo, T.; Stevens, C. V. J. Chem. Soc., Chem. Commun. 2002, 250. (c) Rammeloo, T.; Stevens, C. V.; De Kimpe, N. J. Org. Chem. 2002, 67, 6509. (d) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187. (e) Rammeloo, T.; Stevens, C. V. New J. Chem. 2003, 27, 668. For additional photochemical approaches to 2-azabicyclo[2.1.1]hexanes, see: (f) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. (h) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165.
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25. Calculations using the restricted Hartree-Fock method with the 6-31G(d) basis set show that the aziridinium ion i is 34.6 kcal/mol more stable than the protonated epoxide ii. See Supporting Information.
26. 6 not present in 9. See ref 6.
27. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.
28. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.
29. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.
30. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.
31. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.
32. Silver and mercury salts accelerate substitution reactions of iodides and bromides. (a) Filippo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 782. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 318. (c) Pocker, Y.; Wong, Y.-H. J. Am. Chem. Soc. 1975, 97, 7105. (d) Zamashchikov, V. V.; Rudakov, E. S.; Bezbozhnaya, T. V. React. Kinet. Catal. Lett. 1984, 24, 65. (e) Carreno, M. C.; Carretero, J. C.; Garcia Ruano, J. L.; Rodriguez, J. H. Tetrahedron 1990, 46, 5649-64. (f) Sandler, S. R. J. Org. Chem. 1967, 32, 3876.