Lewis acid-mediated [3+2] cycloaddition between hydrazones and olefins

Tetrahedron Letters

Volumn 44, Issue 16, 2003, Pages 3351-3354

  Kobayashi, Shu ^a   Hirabayashi, Ryoji ^a   Shimizu, Haruka ^a   Ishitani, Haruro ^a   Yamashita, Yasuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Hydrazone; Intermolecular; Intramolecular; Lewis acid; 3+2 cycloaddition

Indexed keywords

ALKENE DERIVATIVE; HYDRAZONE DERIVATIVE; LEWIS ACID; SCANDIUM; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0037436907     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00606-3     Document Type: Article

References (22)

1. Review: Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 3.
2. Reviews: (a) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: Chichester, 1984; Vol. 2, p. 83; (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
3. Reviews: (a) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: Chichester, 1984; Vol. 2, p. 83; (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
4. Reviews: (a) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: Chichester, 1984; Vol. 2, p. 83; (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
5. [3+2] cycloaddition of N-alkylidene 2-aminoesters in the presence of Lewis acid was reported. (a) Grigg, R.; Gunaratne, H. Q. N.; Sridharan, V. Tetrahedron 1987, 43, 5887; (b) Barr, D. A.; Grigg, R.; Gunaratne, H. Q. N.; Kemp, J.; McMeekin, P.; Sridharan, V. Tetrahedron 1988, 44, 557; (c) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384. See also Ref. 2.
6. [3+2] cycloaddition of N-alkylidene 2-aminoesters in the presence of Lewis acid was reported. (a) Grigg, R.; Gunaratne, H. Q. N.; Sridharan, V. Tetrahedron 1987, 43, 5887; (b) Barr, D. A.; Grigg, R.; Gunaratne, H. Q. N.; Kemp, J.; McMeekin, P.; Sridharan, V. Tetrahedron 1988, 44, 557; (c) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384. See also Ref. 2.
7. [3+2] cycloaddition of N-alkylidene 2-aminoesters in the presence of Lewis acid was reported. (a) Grigg, R.; Gunaratne, H. Q. N.; Sridharan, V. Tetrahedron 1987, 43, 5887; (b) Barr, D. A.; Grigg, R.; Gunaratne, H. Q. N.; Kemp, J.; McMeekin, P.; Sridharan, V. Tetrahedron 1988, 44, 557; (c) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384. See also Ref. 2.
8. Hesse K.-D. Liebigs Ann. Chem. 743:1970;50.
9. Grigg R., Kemp J., Thompson N. Tetrahedron Lett. 19:1978;2827.
10. Grigg R., Dowling M., Jordan M. W., Sridharan V. Tetrahedron. 43:1987;5873.
11. Other examples under acidic conditions, see: (a) Fevre, G. L.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; (b) Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; (c) Shimizu, T.; Hayashi, Y.; Ishikawa, S.; Teramura, K. Bull. Chem. Soc. Jpn. 1982, 55, 2456; (d) Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura K. J. Org. Chem. 1987, 52, 2277.
12. Other examples under acidic conditions, see: (a) Fevre, G. L.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; (b) Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; (c) Shimizu, T.; Hayashi, Y.; Ishikawa, S.; Teramura, K. Bull. Chem. Soc. Jpn. 1982, 55, 2456; (d) Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura K. J. Org. Chem. 1987, 52, 2277.
13. Other examples under acidic conditions, see: (a) Fevre, G. L.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; (b) Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; (c) Shimizu, T.; Hayashi, Y.; Ishikawa, S.; Teramura, K. Bull. Chem. Soc. Jpn. 1982, 55, 2456; (d) Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura K. J. Org. Chem. 1987, 52, 2277.
14. Other examples under acidic conditions, see: (a) Fevre, G. L.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; (b) Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; (c) Shimizu, T.; Hayashi, Y.; Ishikawa, S.; Teramura, K. Bull. Chem. Soc. Jpn. 1982, 55, 2456; (d) Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura K. J. Org. Chem. 1987, 52, 2277.
15. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
16. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
17. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
18. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
19. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
20. Other examples under thermal (high pressure) conditions, see: (a) Snider, B. B.; Conn, R. S. E.; Sealfon, S. J. Org. Chem. 1979, 44, 218; (b) Fevre, G. L.; Hamelin, J. Tetrahedron Lett. 1979, 20, 1757; (c) Ibrahim, Y. A.; Abdou, S. E.; Selim, S. Heterocycles 1982, 19, 819; (d) Badawy, M. A.; El-Bahaie, S. A.; Kadry, A. M.; Ibrahim, Y. A. Heterocycles 1988, 27, 7; (e) Khau, V. V.; Martinelli, M. J. Tetrahedron Lett. 1996, 37, 4323; Intramolecular [3+2] cycloaddition of hydrazones under milder conditions: (f) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
21. Kobayashi S., Shimizu H., Yamashita Y., Ishitani H., Kobayashi J. J. Am. Chem. Soc. 124:2002;13678.
22. The relative configuration of 5α was determined by X-ray crystal structure analysis of hydrogenated 5α (8).