The Epoxy-Ramberg-Backlund reaction: A new route to allylic alcohols

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3055-3058

  Evans, Paul ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; EPOXIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030994012     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00507-8     Document Type: Article

References (24)

1. Ramberg, L. ; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A, 1 (Chem. Abstr., 1940, 34, 4725).
2. Ramberg, L. ; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A, 1 (Chem. Abstr., 1940, 34, 4725).
3. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991; Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp 273-284.
4. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991; Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp 273-284.
5. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991; Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp 273-284.
6. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991; Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp 273-284.
7. For a review see Meyers, C.Y.; Malte, A. M.; Matthews, W. S. Quart. Rep. Sulfur Chem. 1970, 5, 229; see also Chan, T. L.; Fong, S.; Li, Y.; Man, T. O.; Poon, C. D. J. Chem. Soc., Chem. Commun. 1994, 1771 and references therein.
8. For a review see Meyers, C.Y.; Malte, A. M.; Matthews, W. S. Quart. Rep. Sulfur Chem. 1970, 5, 229; see also Chan, T. L.; Fong, S.; Li, Y.; Man, T. O.; Poon, C. D. J. Chem. Soc., Chem. Commun. 1994, 1771 and references therein.
9. See, for example, Block, E.; Aslam, M.; Eswarakrishnan, V.; Gebreyes, K.; Hutchinson, J.; Iyer, R.; Laffitte, J. A.; Wall, A. J. Am. Chem. Soc. 1986, 108, 4568; Grumann, A.; Marley, H.; Taylor, R. J. K. Tetrahedron Lett. 1995, 36, 7767 and references therein.
10. See, for example, Block, E.; Aslam, M.; Eswarakrishnan, V.; Gebreyes, K.; Hutchinson, J.; Iyer, R.; Laffitte, J. A.; Wall, A. J. Am. Chem. Soc. 1986, 108, 4568; Grumann, A.; Marley, H.; Taylor, R. J. K. Tetrahedron Lett. 1995, 36, 7767 and references therein.
11. See, for example, Casy, G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317.
12. See, for example, Casy, G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317.
13. Meyers, C. Y.; Hua, D. H.; Peacock, N. J. J. Org. Chem. 1980, 45, 1719.
14. See, for example, Hendrickson, J. B.; Palumbo, P. S. J. Org. Chem. 1985, 50, 2110; Matsuyama, H.; Miyazawa, Y.; Takei, Y.; Kobayashi, M. J. Org. Chem. 1987, 52, 1703; Scarpetti, D.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 8084 and references therein.
15. See, for example, Hendrickson, J. B.; Palumbo, P. S. J. Org. Chem. 1985, 50, 2110; Matsuyama, H.; Miyazawa, Y.; Takei, Y.; Kobayashi, M. J. Org. Chem. 1987, 52, 1703; Scarpetti, D.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 8084 and references therein.
16. See, for example, Hendrickson, J. B.; Palumbo, P. S. J. Org. Chem. 1985, 50, 2110; Matsuyama, H.; Miyazawa, Y.; Takei, Y.; Kobayashi, M. J. Org. Chem. 1987, 52, 1703; Scarpetti, D.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 8084 and references therein.
17. For a discussion of the 1,4-dioxa-system see Crandall, J. K.; Batal, D. J. J. Org. Chem. 1988, 53, 1338 and references therein.
18. For a summary of synthetic routes to α,β-epoxysulfones see Simpkins, N. S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp 55-60, and references therein.
19. 13C-NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
20. Meth-Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. 1 1988, 2663; see also Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897.
21. Meth-Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. 1 1988, 2663; see also Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897.
22. When potassium t-butoxide (2 equiv., THF) was employed in the rearrangement of (1) at RT, 1,3-diphenylpropan-1-one was obtained in 71% yield; this rearrangement of (2) is known (Nomura, H. Bull. Soc. Chim. Fr., 1925, 37, 1246).
23. Nalesnik, T. E.; Fish, J. G.; Horgan, S. W.; Orchin, M. J. Org. Chem. 1981, 46, 1987; Tanno, N.; Terashima, S. Chem. Pharm. Bull. 1983, 31, 837.
24. Nalesnik, T. E.; Fish, J. G.; Horgan, S. W.; Orchin, M. J. Org. Chem. 1981, 46, 1987; Tanno, N.; Terashima, S. Chem. Pharm. Bull. 1983, 31, 837.