Efficient Diastereoselective Syntheses of erythro- Or threo-a-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCI4/BHg or LiEtsBH/CeCl3, Respectively

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3624-3630

  Marcantoni, Enrico ^a   Cingolani, Simone ^a   Bartoli, Giuseppe ^b   Bosco, Marcella ^b   Sambri, Letizia ^b  

^a Dipartimento di Scienze Chimiche   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001373323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972284k     Document Type: Article

References (47)

1. Recent overview: Trost, B. M. Bull. Chem. Soc. Jpn. 1988, 61, 107.
2. Magnus, P. D. Tetrahedron 1977, 33, 2019.
3. Schank, K. Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Thieme: Stuttgart, 1985; Vol. E11, p 1129.
4. Durst, T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, pp 171-197.
5. The Chemistry of Sulfones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; pp 1-1210.
6. Fuchs, P. L.; Breish, T. F. Chem. Rev. 1986, 86, 903.
7. For an excellent review on sulfone-based olefination reactions (Julia olefination), see: Kocienski, P. Phosphorus Sulfur Relat. Elem. 1985, 24, 97-127. See also: Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833. Hird, N. W.; Lee, T. V.; Leigh, A. J.; Maxwell, J. R.; Peakman, T. M. Tetrahedron Lett. 1989, 30, 4867.
8. For an excellent review on sulfone-based olefination reactions (Julia olefination), see: Kocienski, P. Phosphorus Sulfur Relat. Elem. 1985, 24, 97-127. See also: Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833. Hird, N. W.; Lee, T. V.; Leigh, A. J.; Maxwell, J. R.; Peakman, T. M. Tetrahedron Lett. 1989, 30, 4867.
9. For an excellent review on sulfone-based olefination reactions (Julia olefination), see: Kocienski, P. Phosphorus Sulfur Relat. Elem. 1985, 24, 97-127. See also: Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833. Hird, N. W.; Lee, T. V.; Leigh, A. J.; Maxwell, J. R.; Peakman, T. M. Tetrahedron Lett. 1989, 30, 4867.
10. Williams, D. R.; Harigaya, Y.; Moore, J. L.; D'sa, A. J. Am. Chem. Soc. 1984, 106, 2641.
11. Noda, I.; Horita, K.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 1917.
12. Brussani, G.; Ley, S. V.; Wright, J. L.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1986, 303.
13. Bartlett, P. A. Tetrahedron 1980, 36, 46.
14. Kondo, K.; Matsumoto, M. Tetrahedron Lett. 1976, 17, 4364.
15. Kocienski, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 987.
16. Hart, D. J.; Wu, W. L. Tetrahedron Lett. 1996, 37, 5283.
17. Julia, M.; Launay, M.; Stacino, J.-P.; Verpeaux, J.-N. Tetrahedron Lett 1982, 23, 2465.
18. Grossert, J. S.; Dharmaratue, H. R. W.; Cameron, T. S.; Vincent, B. R. Can. J. Chem. 1988, 66, 2860.
19. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 1997, 12, 1941.
20. Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem 1996, 61, 868.
21. (a) Chérest, M.; Felkin, H.; Prudent, N. Tetrhedron Lett. 1968, 2199.
22. (b) Anh, N. T.; Einsenstein, O. Nouv. J. Chim. 1977, 1, 61.
23. Bordwell, F. G.; Van Der Puy, M.; Vanier, N. R. J. Org. Chem. 1916, 41, 1883.
24. 3 prepared by the present procedure; however, the material was highly efficient without a large excess of reducing agent.
25. (a) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. J. Am. Chem. Soc. 1973, 95, 5065.
26. (b) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563.
27. Bürgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956.
28. Bartoli, G.; Bosco, M.; Marcantoni, E.; Sambri, L. Tetrahedron Lett. 1996, 37, 7421.
29. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1.
30. Fukuzawa, S.; Fujinami, T.; Yamanchi, S.; Sakai, S. J. Chem. Soc., Perkin Trans, 1 1986, 1929.
31. To avoid ambiguity when indicating the hydroxy sulfones 5 we will follow the relative position of hydroxy group and α-ethyl group.
32. Bohlmann, F.; Haffer, G. Chem. Ber. 1969, 102, 4017.
33. Grossert, J. S.; Dharmaratne, H. R. W.; Cameron, T. S.; Vincent, B. R. Can. J. Chem. 1988, 66, 2860.
34. Reinach-Hirtzbach, F.; Durst, T. Tetrahedron Lett. 1976, 3677.
35. Scholz, D. Chem. Ber. 1981, 114, 909.
36. Grossert, J. S.; Dubey, P. K.; Elwood, T. Can. J. Chem. 1985, 63, 1263.
37. Harding, K. E.; Toner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I, Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 363-415.
38. Ireland, R. E.; Habich, D.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3971
39. Ueno, Y.; Khare, R. K.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1983, 2637.
40. O'Sullivan, W. I.; Tavares, D. F.; Hauser, C. R. J. Am. Chem. Soc. 1961, 83, 3453.
41. Ezquerra, J.; Alvarez-Builla, J. J. Chem. Soc., Chem. Commun. 1984, 54.
42. Trost, B. M.; Lynch, J.; Renaut, P.; Steinman, D. H. J. Am. Chem. Soc. 1986, 108, 284.
43. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
44. Anderson, M. B.; Fuchs, P. L. Synth. Commun. 1987, 17, 621.
45. Imamoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 231-250.
46. Crandall, J. K.; Pradat, C. J. Org. Chem. 1985, 50, 1327.
47. Descriptors R*,S* indicate that diastereomeric compounds are obtained as racemates. We prefer this terminology to avoid the ambiguities that could arise from thp use of erythro.threo.