Concise Synthesis of Optically Pure syn-1,3-Diols by Stereoselective Desymmetrization of a Divinylcarbinol

Synlett

Volumn , Issue 12, 2003, Pages 1813-1816

  Berkenbusch, Thilo ^a   Brückner, Reinhard ^b  

^a BAYER AG   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

1,3 diols; Acetonides; Desymmetrization; Epoxyalcohols; Sharpless asymmetric epoxidation

Indexed keywords

ALCOHOL DERIVATIVE; DIVINYLCARBINOL; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; HIGH TEMPERATURE; STEREOCHEMISTRY;

EID: 0142060653     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41487     Document Type: Article

References (64)

1. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
2. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
3. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
4. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
5. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
6. For leading references on asymmetric desymmetrizations of substrates containing no stereocenter, see: (a) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. (c) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273. (e) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem. Int. Ed. 2003, 42, 1734; Angew. Chem. 2003, 115, 1776.
7. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
8. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
9. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
10. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
11. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
12. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
13. For leading references on asymmetric desymmetrizations of substrates, which are meso-configured, see: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. (d) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995. (e) Katsuki, T. Curr. Org. Chem. 2001, 5, 663. (f) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080. (g) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226.
14. (a) Schreiber, S. L. Chem. Scr. 1987, 27, 563.
15. (b) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1.
16. (c) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
17. (d) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim New York, 1995, 203.
18. (e) Magnuson, S. R. Tetrahedron 1995, 51, 2167.
19. (f) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
20. (g) Hoffmann, R. W. Angew. Chem. Int. Ed. 2003, 42, 1096; Angew. Chem. 2003, 115, 1128.
21. (g) Hoffmann, R. W. Angew. Chem. Int. Ed. 2003, 42, 1096; Angew. Chem. 2003, 115, 1128.
22. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
23. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
24. (a) Hatakeyama, S.; Sakurai, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1985, 1759.
25. (b) Häfele, B.; Schröter, D.; Jäger, V. Angew. Chem. Int. Ed. Engl. 1986, 25, 87; Angew. Chem. 1986, 98, 89.
26. (b) Häfele, B.; Schröter, D.; Jäger, V. Angew. Chem. Int. Ed. Engl. 1986, 25, 87; Angew. Chem. 1986, 98, 89.
27. (c) Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525.
28. (d) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793.
29. (e) Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583.
30. (f) Jäger, V.; Hümmer, W.; Stahl, U.; Gracza, T. Synthesis 1991, 769.
31. Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201.
32. (a) Herunsalee, A.; Isobe, M.; Pikul, S.; Goto, T. Synlett 1991, 199.
33. (b) Hatakeyama, S.; Satoh, K.; Takano, S. Tetrahedron Lett. 1993, 34, 7425.
34. (c) Esumi, T.; Fukuyama, H.; Oribe, R.; Kawazoe, K.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1997, 38, 4823.
35. (d) Nishioka, T.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 5597.
36. (a) Omura, S.; Tanaka, H. In Macrolide Antibiotics: Chemistry, Biology and Practice; Omura, S., Ed.; Academic Press: New York, 1984, 351-404.
37. (b) Oishi, T.; Nakata, T. Synthesis 1990, 635.
38. (c) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
39. (d) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445.
40. (d) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445.
41. 7a
42. 1H NMR and IR spectra as well as correct combustion analyses.
43. (a) Rieke, R. D.; Uhm, S. J.; Hudnall, P. M. J. Chem. Soc., Chem. Commun. 1973, 269.
44. (b) Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
45. Procedure: (a) Avignon-Tropis, M.; Pougny, J. R. Tetrahedron Lett. 1989, 30, 4951. (b) Chou, W.-N.; Clark, D. L.; White, J. B. Tetrahedron Lett. 1991, 32, 299.
46. Procedure: (a) Avignon-Tropis, M.; Pougny, J. R. Tetrahedron Lett. 1989, 30, 4951. (b) Chou, W.-N.; Clark, D. L.; White, J. B. Tetrahedron Lett. 1991, 32, 299.
47. (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I. E., Ed.; Wiley-VCH: New York, 1993, 103-158.
48. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1.
49. SAEs of cis-2-butene-1,4-diol mono-protected with a tertbutyldimethylsilyl roup: (a) Astles, P. C.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1997, 845; 85% ee. (b) Shibuya, H.; Kawashima, K.; Narita, N.; Ikeda, M.; Kitagawa, I. Chem. Pharm. Bull. 1992, 40, 1154; 84-85% ee.
50. SAEs of cis-2-butene-1,4-diol mono-protected with a tertbutyldimethylsilyl roup: (a) Astles, P. C.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1997, 845; 85% ee. (b) Shibuya, H.; Kawashima, K.; Narita, N.; Ikeda, M.; Kitagawa, I. Chem. Pharm. Bull. 1992, 40, 1154; 84-85% ee.
51. SAEs of cis-2-butene-1,4-diol mono-protected with a PMB group: (a) Williams, R. M.; Rollins, S. B.; Judd, T. C. Tetrahedron 2000, 56, 521; 88% ee. (b) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239; 85% ee.
52. SAEs of cis-2-butene-1,4-diol mono-protected with a PMB group: (a) Williams, R. M.; Rollins, S. B.; Judd, T. C. Tetrahedron 2000, 56, 521; 88% ee. (b) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239; 85% ee.
53. minor = 3.08(dd)].
54. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
55. In addition, we retrieved inseparable mixtures of mono- with bis-epoxides.
56. minor = 3.08(dd)].
57. Moreover, tert-butyldimethylsiloxy groups do not withstand prolonged exposure to Red-Al®: Berkenbusch, T. PhD Dissertation; Universität Freiburg: Germany, 2002.
58. Regioselective reductions of α,β-epoxy alcohols resulting in 1,3-diols (Red-Al®-method) or 1,2-diols (DIBAL-method): (a) Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719. (b) Viti, S. M. Tetrahedron Lett. 1982, 23, 4541.
59. Regioselective reductions of α,β-epoxy alcohols resulting in 1,3-diols (Red-Al®-method) or 1,2-diols (DIBAL-method): (a) Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719. (b) Viti, S. M. Tetrahedron Lett. 1982, 23, 4541.
60. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
61. (b) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
62. (c) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
63. 4, D-(-)-diisopropyl tartrate, and t-BuOOH is described in: Spivey, A. C.; Woodhead, S. J.; Weston, M.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 769; Angew. Chem. 2001, 113, 191.
64. 4, D-(-)- diisopropyl tartrate, and t-BuOOH is described in: Spivey, A. C.; Woodhead, S. J.; Weston, M.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 769; Angew. Chem. 2001, 113, 191.