Chiral base-mediated rearrangement of meso-cyclohexene oxides to allylic alcohols

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8057-8058

  O'Brien, Peter ^a   Poumellec, Pierre ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; CYCLOHEXENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01824-2     Document Type: Article

References (26)

1. 1. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron, 1996, 52, 3769-3826.
2. 2. Ward, R. S. Chem. Soc. Rev., 1990, 19, 1-19; Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl., 1992, 31, 1179-1180; Ramón, D. J.; Guillena, G.; Seebach, D. Helv. Chim. Acta, 1996, 79, 875-893.
3. 2. Ward, R. S. Chem. Soc. Rev., 1990, 19, 1-19; Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl., 1992, 31, 1179-1180; Ramón, D. J.; Guillena, G.; Seebach, D. Helv. Chim. Acta, 1996, 79, 875-893.
4. 2. Ward, R. S. Chem. Soc. Rev., 1990, 19, 1-19; Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl., 1992, 31, 1179-1180; Ramón, D. J.; Guillena, G.; Seebach, D. Helv. Chim. Acta, 1996, 79, 875-893.
5. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
6. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
7. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
8. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
9. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
10. 3. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 1402-1408; Asami, M.; Inoue, S. Tetrahedron, 1995, 51, 11725-11730; Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun., 1993, 884-886; Hodgson, D. M.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337-338; Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850; Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry, 1994, 5, 1649-1652.
11. 4. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70; Mori, K.; Murata, N. Liebigs Ann. Chem., 1995, 2089-2092. Asami's chiral base: Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 721-727.
12. 4. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70; Mori, K.; Murata, N. Liebigs Ann. Chem., 1995, 2089-2092. Asami's chiral base: Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 721-727.
13. 4. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70; Mori, K.; Murata, N. Liebigs Ann. Chem., 1995, 2089-2092. Asami's chiral base: Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 721-727.
14. 5. Bhuniya, D.; Singh, V. K. Synth. Commun., 1994, 24, 1475-1481.
15. 6. For synthesis of the corresponding amine, see: O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 5619-5622.
16. 7. Krow, G. R.; Carmosin, R.; Mancuso, A. Org. Prep. Proc. Int., 1977, 9, 285-288.
17. 8. Tschamber, T.; Backenstrass, F.; Fritz, H.; Streith, J. Helv. Chim. Acta, 1992, 75, 1052-1060.
18. 9. Alvarez, E.; Díaz, M. T.; Pérez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martín, J. D. J. Org. Chem., 1994, 59, 2848-2876.
19. 10. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem., 1969, 34, 2543-2549.
20. 11. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4096; Pehk, T.; Lippmaa, E.; Lopp, M.; Paju, A.; Borer, B. C.; Taylor, R. J. K. Tetrahedron: Asymmetry, 1993, 4, 1527-1532.
21. 11. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4096; Pehk, T.; Lippmaa, E.; Lopp, M.; Paju, A.; Borer, B. C.; Taylor, R. J. K. Tetrahedron: Asymmetry, 1993, 4, 1527-1532.
22. 12. Colas, C.; Quiclet-Sire, B.; Cléophax, J.; Delaumény, J-M.; Sepulchre, A-M.; Géro, S. D. J. Am. Chem. Soc., 1980, 702, 857-858; Andia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem., 1989, 54, 3738-3740; Reddy, K. K.; Falck, J. R.; Capdevila, J. Tetrahedron Lett., 1993, 34, 7869-7872; Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem., 1994, 59, 5596-5608; Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett., 1994, 35, 4279-4282.
23. 12. Colas, C.; Quiclet-Sire, B.; Cléophax, J.; Delaumény, J-M.; Sepulchre, A-M.; Géro, S. D. J. Am. Chem. Soc., 1980, 702, 857-858; Andia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem., 1989, 54, 3738-3740; Reddy, K. K.; Falck, J. R.; Capdevila, J. Tetrahedron Lett., 1993, 34, 7869-7872; Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem., 1994, 59, 5596-5608; Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett., 1994, 35, 4279-4282.
24. 12. Colas, C.; Quiclet-Sire, B.; Cléophax, J.; Delaumény, J-M.; Sepulchre, A-M.; Géro, S. D. J. Am. Chem. Soc., 1980, 702, 857-858; Andia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem., 1989, 54, 3738-3740; Reddy, K. K.; Falck, J. R.; Capdevila, J. Tetrahedron Lett., 1993, 34, 7869-7872; Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem., 1994, 59, 5596-5608; Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett., 1994, 35, 4279-4282.
25. 12. Colas, C.; Quiclet-Sire, B.; Cléophax, J.; Delaumény, J-M.; Sepulchre, A-M.; Géro, S. D. J. Am. Chem. Soc., 1980, 702, 857-858; Andia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem., 1989, 54, 3738-3740; Reddy, K. K.; Falck, J. R.; Capdevila, J. Tetrahedron Lett., 1993, 34, 7869-7872; Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem., 1994, 59, 5596-5608; Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett., 1994, 35, 4279-4282.
26. 12. Colas, C.; Quiclet-Sire, B.; Cléophax, J.; Delaumény, J-M.; Sepulchre, A-M.; Géro, S. D. J. Am. Chem. Soc., 1980, 702, 857-858; Andia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem., 1989, 54, 3738-3740; Reddy, K. K.; Falck, J. R.; Capdevila, J. Tetrahedron Lett., 1993, 34, 7869-7872; Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem., 1994, 59, 5596-5608; Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett., 1994, 35, 4279-4282.