Aluminum Tris(4-bromo-2,6-diphenylphenoxide)(ATPH-Br): An Effective Catalyst for Claisen Rearrangement

Synlett

Volumn 1996, Issue 8, 1996, Pages 720-722

  Saito, Susumu ^a   Shimada, Kazuto ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001983556     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5517     Document Type: Article

References (36)

1. (a) Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131.
2. (b) Maruoka, K.; Imoto, H.; Yamamoto, H. ibid. 1994, 116, 12115.
3. (c) Maruoka, K.; Akakura, M.; Yamamoto, H. Synlett 1995, 81. ATPH for Claisen rearrangement :
4. (d) Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
5. (e) Maruoka, K.; Ito, M.; Yamamoto, H. ibid. 1995, 117, 9091.
6. (a) Maruoka, K.; Ooi, T; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431.
7. (b) Maruoka, K.; Ooi, T.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 5607.
8. (c) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 9011.
9. (d) Maruoka, K.; Sato, J.; Yamamoto, H.; ibid. 1993, 113, 5449.
10. (e) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983.
11. (f) Maruoka, K.; Shiohara, K.; Oishi, M.; Saito, S.; Yamamoto, H. Synlett 1993, 421.
12. (g) Ishihara, K.; Funahashi, M.; Hanaki, M.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
13. (h) Mikami, K.; Motoyama, Y.; Terada, M. Inorg. Chem. Acta. 1994, 222, 71.
14. (i) Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693.
15. (j) Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1995, 721.
16. (k) Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1995, 2391.
17. Claisen rearrangement using a stoichiometric amount of MABR : (a) Maruoka, K.; Nonoshita, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 7922. (b) Maruoka, K.; Sato, J.; Banno, H.; Yamamoto, H. Tetrahedron Lett. 1990, 31, 377. MABR for stereoselective carbon-carbon formation reactions : see also ref. 2.
18. Claisen rearrangement using a stoichiometric amount of MABR : (a) Maruoka, K.; Nonoshita, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 7922. (b) Maruoka, K.; Sato, J.; Banno, H.; Yamamoto, H. Tetrahedron Lett. 1990, 31, 377. MABR for stereoselective carbon-carbon formation reactions : see also ref. 2.
19. (a) Maruoka, K.; Araki, Y.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 2650.
20. (b) Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
21. (c) Maruoka, K.; Nagahara, S.; Yamamoto, H. ibid. 1990, 112, 6225.
22. (d) Maruoka, K.; Nagahara, S.; Yamamoto, H. Tetrahedron Lett. 1990, 31, 5475.
23. (e) Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1992, 114, 1089.
24. The E/Z ratio was determined by GC analysis against authentic samples after converting the obtained products into the corresponding alcohols or their silyl ethers: See ref. 3a.
25. 3, 75 MHz): Inverse-gated experiment with a relaxation delay of 4 s, an acquisition time of 3.2 s, and a pulse angle of 45°. The obtained E/Z ratio was in accord with that obtained from GC analysis.
26. Thermal Claisen rearrangement of allylic tertiary alcohol derivatives: (a) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253. (b) Saucy, G.; Marbet, R. Helv. Chim. Acta. 1967, 50, 2019.
27. Thermal Claisen rearrangement of allylic tertiary alcohol derivatives: (a) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253. (b) Saucy, G.; Marbet, R. Helv. Chim. Acta. 1967, 50, 2019.
28. Lewis acid-promoted intramolecular ene reaction: (a) Snider, B. B.; Deutsch, E. A. J. Org. Chem. 1983, 48, 1822. (b) Johnson, M. I.; Kwass, A. J.; Beal, R. B.; Snider, B. B. ibid. 1987, 52, 5419. (c) Snider, B. B.; Allentoff, A. J.; Kulkarni, Y. S. ibid. 1988, 53, 5320. (d) Marshall, J. A.; Anderson, M. W. ibid. 1992, 57, 5851. (e) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 7701. The stereoselective intramolecular ene reaction of δ,ε-unsaturated aldehydes promoted by MABR has been reported : see ref. 2c.
29. Lewis acid-promoted intramolecular ene reaction: (a) Snider, B. B.; Deutsch, E. A. J. Org. Chem. 1983, 48, 1822. (b) Johnson, M. I.; Kwass, A. J.; Beal, R. B.; Snider, B. B. ibid. 1987, 52, 5419. (c) Snider, B. B.; Allentoff, A. J.; Kulkarni, Y. S. ibid. 1988, 53, 5320. (d) Marshall, J. A.; Anderson, M. W. ibid. 1992, 57, 5851. (e) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 7701. The stereoselective intramolecular ene reaction of δ,ε-unsaturated aldehydes promoted by MABR has been reported : see ref. 2c.
30. Lewis acid-promoted intramolecular ene reaction: (a) Snider, B. B.; Deutsch, E. A. J. Org. Chem. 1983, 48, 1822. (b) Johnson, M. I.; Kwass, A. J.; Beal, R. B.; Snider, B. B. ibid. 1987, 52, 5419. (c) Snider, B. B.; Allentoff, A. J.; Kulkarni, Y. S. ibid. 1988, 53, 5320. (d) Marshall, J. A.; Anderson, M. W. ibid. 1992, 57, 5851. (e) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 7701. The stereoselective intramolecular ene reaction of δ,ε-unsaturated aldehydes promoted by MABR has been reported : see ref. 2c.
31. Lewis acid-promoted intramolecular ene reaction: (a) Snider, B. B.; Deutsch, E. A. J. Org. Chem. 1983, 48, 1822. (b) Johnson, M. I.; Kwass, A. J.; Beal, R. B.; Snider, B. B. ibid. 1987, 52, 5419. (c) Snider, B. B.; Allentoff, A. J.; Kulkarni, Y. S. ibid. 1988, 53, 5320. (d) Marshall, J. A.; Anderson, M. W. ibid. 1992, 57, 5851. (e) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 7701. The stereoselective intramolecular ene reaction of δ,ε-unsaturated aldehydes promoted by MABR has been reported : see ref. 2c.
32. Lewis acid-promoted intramolecular ene reaction: (a) Snider, B. B.; Deutsch, E. A. J. Org. Chem. 1983, 48, 1822. (b) Johnson, M. I.; Kwass, A. J.; Beal, R. B.; Snider, B. B. ibid. 1987, 52, 5419. (c) Snider, B. B.; Allentoff, A. J.; Kulkarni, Y. S. ibid. 1988, 53, 5320. (d) Marshall, J. A.; Anderson, M. W. ibid. 1992, 57, 5851. (e) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 7701. The stereoselective intramolecular ene reaction of δ,ε-unsaturated aldehydes promoted by MABR has been reported : see ref. 2c.
33. 3, 300 MHz) 8a: δ 3.71 (ddd, 1H, J = 10.4, 10.4, 3.9 Hz, CHOH); 8b: δ 3.60 (ddd, 1H, J = 10.4, 10.4, 4.2 Hz, CHOH). The stereochemical relationship between the quaternary carbon and the hydroxyl-attached carbon was determined by NOESY measurement as illustrated below. (Matrix Presented)
34. 1H NMR analysis.
35. Thermal Claisen rearrangement of allylic secondary alcohol derivatives : (a) Brannock, K. C. J. Am. Chem. Soc. 1959, 81, 3379. (b) Faulkner, D. J.; Peterson, M. R. Tetrahedron Lett. 1969, 3243.
36. Thermal Claisen rearrangement of allylic secondary alcohol derivatives : (a) Brannock, K. C. J. Am. Chem. Soc. 1959, 81, 3379. (b) Faulkner, D. J.; Peterson, M. R. Tetrahedron Lett. 1969, 3243.