Enantioselective Ring Opening of Epoxides with Silicon Tetrachloride in the Presence of a Chiral Lewis Base

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2428-2429

  Denmark, Scott E ^a   Barsanti, Paul A ^a   Wong, Ken Tsung ^a   Stavenger, Robert A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000048225     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801420     Document Type: Article

References (35)

1. (a) Erden, I. In Comprehensive Heterocyclic Chemistry, 2nd ed.; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 1A, Chapter 1.03.
2. (b) Bartók, M.; Lang, K. L. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1985; Vol. 42, Part 3, p 1.
3. (c) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
4. (a) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis, Vol. 7, Oxidation; Ley, S. V., Ed.; Pergamon Press: Oxford, 1991; Chapter 3.2.
5. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Chapter 4.1.
6. (c) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Chapter 4.2.
7. For leading references of enantioselective ring opening of epoxides, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (c) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. For a recent review see: (e) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
8. For leading references of enantioselective ring opening of epoxides, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (c) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. For a recent review see: (e) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
9. For leading references of enantioselective ring opening of epoxides, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (c) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. For a recent review see: (e) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
10. For leading references of enantioselective ring opening of epoxides, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (c) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. For a recent review see: (e) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
11. For leading references of enantioselective ring opening of epoxides, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (c) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. For a recent review see: (e) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
12. Bonini, C.; Righi, G. Synthesis 1994, 225.
13. Halohydrins also serve as important synthetic intermediates in their own right and are critical subunits for the synthesis of halogenated marine natural products. For reviews see: Fenical, W. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1980; Vol. 2, p 174.
14. Cross, A. D. Quart. Rev. Chem Soc. 1960, 14, 317.
15. (a) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246.
16. (b) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747.
17. (a) Andrews, G. C.; Crawford, T. C.; Contillo, L. G., Jr. Tetrahedron Lett. 1981, 22, 3803.
18. (b) Garrett, C. E.; Fu, G. C. J. Org. Chem. 1997, 62, 4534.
19. Silicon tetrafluoride has been used together with Hünig base to open epoxides. Shimizu, M.; Yoshioka, H. Tetrahedron Lett. 1988, 29, 4101.
20. (a) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
21. (b) Denmark, S. E.; Winter, S. B. D. Synlett 1997, 1087.
22. (c) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333.
23. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918.
24. 4 steps. The boat-twist chair was found to be the global minimum with six similar conformations within 1.6 kJ/mol.
25. Garner, P.; Park, J. M. Synth. Commun. 1987, 27, 189.
26. (a) For compounds 10, 11, 13, 15, and 16, see ref 8b.
27. (b) Compound 12: Allinger, N. L.; Tushaus, L. A. Tetrahedron 1967, 23, 2051.
28. (c) Compound 17: Caputo, R.; Ferrer, C.; Noviello, S.; Palumbo, G. Synthesis 1986, 499.
29. (d) Compound 18: Besse, P.; Renard, M. F.; Veschambre, H. Tetrahedron: Asymmetry 1994, 5, 1249.
30. The regiochemical assignment was confirmed by preparation of the trifluoroacetate of 17 and the acetate of 18.
31. Other promoters examined include the following: phosphoramides based on the stilbenediamine and cyclohexane-1,2-diaznine skeletons, sparteine, nicotine, cinchona alkaloids, chiral oxazolines, and assorted chiral tertiary amines and diamines.
32. 3SiMeCl.
33. 3): Sadozai, S. K; Merckx, E. M.; Van de Wal, A. J.; Lemière, G. L.; Esmans, E. L.; Lepoivre, J. A.; Alderweireldt, F. C. Bull. Chem. Soc. Belg. 1982, 92, 163.
34. D -20.2 (c = 5.2, EtOH): Berti, G.; Bottari, F.; Ferrerini, P. L.; Macchia, B. J. Org. Chem. 1965, 30, 4091.
35. 3PO. Short, J. D.; Attenoux, S.; Berrisford, D. J. Tetrahedron Lett. 1997, 38, 2351.