Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3777-3779

  Gayet, Arnaud ^a   Bertilsson, Sophie ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

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ARTICLE;

EID: 0012317165     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025983e     Document Type: Article

References (21)

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2. (b) Kagan, H. B. Tetrahedron 2001, 57, 2449-2468.
3. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26, and references therein.
4. For earlier studies in this field, see: (a) Mori, K.; Hazra, B. G.; Pfeiffer, R. J.; Gupta, A. K.; Lindgren, B. S. Tetrahedron 1987, 43, 2249-2254. (b) Asami, M.; Kanemaki, N. Tetrahedron Lett. 1989, 30, 2125-2128. Bigi, A.; Mordini, A.; Thurner, A.; Faigl, F.; Poli, G.; Tõke, L. Tetrahedron: Asymmetry 1998, 9, 2293-2299.
5. For earlier studies in this field, see: (a) Mori, K.; Hazra, B. G.; Pfeiffer, R. J.; Gupta, A. K.; Lindgren, B. S. Tetrahedron 1987, 43, 2249-2254. (b) Asami, M.; Kanemaki, N. Tetrahedron Lett. 1989, 30, 2125-2128. Bigi, A.; Mordini, A.; Thurner, A.; Faigl, F.; Poli, G.; Tõke, L. Tetrahedron: Asymmetry 1998, 9, 2293-2299.
6. For earlier studies in this field, see: (a) Mori, K.; Hazra, B. G.; Pfeiffer, R. J.; Gupta, A. K.; Lindgren, B. S. Tetrahedron 1987, 43, 2249-2254. (b) Asami, M.; Kanemaki, N. Tetrahedron Lett. 1989, 30, 2125-2128. Bigi, A.; Mordini, A.; Thurner, A.; Faigl, F.; Poli, G.; Tõke, L. Tetrahedron: Asymmetry 1998, 9, 2293-2299.
7. For reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457. (b) Asami, M. J. Synth. Org. Chem. Jpn. 1996, 54, 188-199. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
8. For reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457. (b) Asami, M. J. Synth. Org. Chem. Jpn. 1996, 54, 188-199. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
9. For reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457. (b) Asami, M. J. Synth. Org. Chem. Jpn. 1996, 54, 188-199. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
10. For reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457. (b) Asami, M. J. Synth. Org. Chem. Jpn. 1996, 54, 188-199. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
11. For the first reports on the different groups of lithium amide bases, see: (a) Asami, M. Chem. Lett. 1984, 829-832. (b) Bhuniya, D.; Singh, V. K. Synth. Commun. 1994, 24, 1475-1481. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-886. Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022.
12. For the first reports on the different groups of lithium amide bases, see: (a) Asami, M. Chem. Lett. 1984, 829-832. (b) Bhuniya, D.; Singh, V. K. Synth. Commun. 1994, 24, 1475-1481. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-886. Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022.
13. For the first reports on the different groups of lithium amide bases, see: (a) Asami, M. Chem. Lett. 1984, 829-832. (b) Bhuniya, D.; Singh, V. K. Synth. Commun. 1994, 24, 1475-1481. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-886. Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022.
14. For the first reports on the different groups of lithium amide bases, see: (a) Asami, M. Chem. Lett. 1984, 829-832. (b) Bhuniya, D.; Singh, V. K. Synth. Commun. 1994, 24, 1475-1481. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-886. Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022.
15. (a) Södergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760-10761.
16. (b) Södergren, M. J.; Bertilsson, S. K.; Andersson, P. G. J. Am. Chem. Soc. 2000, 122, 6610-6618.
17. Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428.
18. Asami, M.; Sato, S.; Honda, K.; Inoue, S. Heterocyde 2000, 3, 1029-1032.
19. The beneficiary effect of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) in the catalytic rearrangement reaction has been shown earlier; see: Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796 and refs 6 and 3c therein.
20. Also, about 10% yield of 2-tert-butylcyclohex-2-en-1-ol was obtained in the reaction.
21. Crandall, J. K.; Lin, L.-H. C. J. Org. Chem. 1968, 33, 2375-2378. See also ref 3a.