Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3324-3332

  García Ruano, Jose L ^a   Gamboa, Antonio Esteban ^a   Martín Castro, Ana M ^a   Rodríguez, Jesús H ^a   López Solera, M Isabel ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001244096     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9721002     Document Type: Article

References (61)

1. (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
2. (b) Carretero, J. C.; García Ruano, J. L.; Martín Cabrejas, L. M. Tetrahedron: Asymmetry 1997, 8, 2215 (and references cited).
3. (c) Carreño, M C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976 (and references cited).
4. (d) Yamakoshi, Y. N.; Ge, W.-Y.; Sugita, J.; Okayama, K.; Takahashi, T.; Koizumi T. Heterocycles 1996, 42, 129 (and references cited).
5. (e) Cecchet, E.; Di Furia, F.; Licini, G.; Modena, G. Tetrahedron: Asymmetry 1996, 7, 369.
6. (f) Hayes, P.; Dujardin, G.; Maignan, C. Tetrahedron Lett. 1996, 21, 3687 (and references cited).
7. (g) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962 (and references cited).
8. (a) Alcudia, F.; Liera, J. M.; Ordoñez, M. Tetrahedron Lett. 1995, 36, 4889.
9. (b) Guessous, A.; Rouesaac, F.; Maignan, C. Bull Soc. Chim. Fr. 1986, 837.
10. (c) De Lucchi, O.; Lucchini, V.; Marchioro, C.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457.
11. (d) Brimble, M. A.; Davis, B. R. Tetrahedron 1985, 41, 4965.
12. Fuji, K.; Tanaka, K.; Abe, H.; Matsumoto, K.; Harayama, T.; Ikeda, A.; Taga, T.; Miwa, Y.; Node, M. J. Org. Chem. 1994, 59, 2221.
13. López, K.; Carreteero, J. C. Tetrahedron: Asymmetry 1991, 2, 93.
14. (a) Arai, Y.; Kuwayama, S.; Takeuchi, Y.; Koizumi, T. Synth. Commun. 1986, 16, 233.
15. (b) De Lucchi, O.; Fabbri, D.; Lucchini, V. Synlett 1991, 565.
16. (c) Aggarwal, V. N.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730.
17. (d) Katagiri, N.; Ise, S.; Watanabe, N.; Kaneko, C. Chem. Pharm. Bull. 1990, 38, 3242.
18. (e) Carretero, J. C.; García Ruano, J. L.; Martín Cabrejas, L. M. Tetrahedron: Asymmetry 1997, 8, 409.
19. See Arai, Y.; Koizumi, T. Sulfur Rep. 1993, 15, 41 (and references cited).
20. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771. The use of sulfoxides bearing bornyl and isobornyl moieties joined to the sulfur atom, which control the asymmetric oxidation of thioethers into sulfoxides, allowed solution of this problem ( De Lucchi, O.; Lucchini, V.; Marchioro, C.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457), but these sulfoxides have never been used in the synthesis of natural products.
21. Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771. The use of sulfoxides bearing bornyl and isobornyl moieties joined to the sulfur atom, which control the asymmetric oxidation of thioethers into sulfoxides, allowed solution of this problem ( De Lucchi, O.; Lucchini, V.; Marchioro, C.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457), but these sulfoxides have never been used in the synthesis of natural products.
22. (a) Koizumi, T.; Hakamada, I.; Yoshii, E. Tetrahedron Lett. 1984, 25, 87.
23. (b) Maignan, C.; Guessoues, A.; Rouessac, F. Tetrahedron Lett. 1984, 25, 1727.
24. Arai, Y.; Kuwayama, S.; Takeuchi, Y.; Koizumi, T. Tetrahedron Lett. 1984, 25, 6205.
25. Proust, S. M.; Ridley, D. D. Aust. J. Chem. 1984, 37, 1677.
26. Arai, Y.; Hayashi, M.; Yamamoto, M.; Takayama, H.; Koizumi, T. Chem. Lett. 1987, 185.
27. Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890. Trost, B. M.; Mallarts, S. Tetrahedron Lett. 1993, 34, 8025. Hiroi, K.; Umemura, M. Tetrahedron 1993, 49, 1831.
28. Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890. Trost, B. M.; Mallarts, S. Tetrahedron Lett. 1993, 34, 8025. Hiroi, K.; Umemura, M. Tetrahedron 1993, 49, 1831.
29. Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890. Trost, B. M.; Mallarts, S. Tetrahedron Lett. 1993, 34, 8025. Hiroi, K.; Umemura, M. Tetrahedron 1993, 49, 1831.
30. The synthesis of optically pure 1-alkynyl p-tolyl sulfoxides 2a-d was accomplished following the previously described procedure (Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078) consisting in the reaction of l-menthyl (S)-p-toluenesulfinate (Mioskowsky, C.; Solladié, G. Tetrahedron 1980, 36, 227. Solladié, G. Synthesis 1981, 185) and the corresponding 1-alkynyl-magnesium bromide in toluene. In our hands, the reaction temperature had to be increased from -20 °C, as described, to 20 °C in order to get good yields.
31. The synthesis of optically pure 1-alkynyl p-tolyl sulfoxides 2a-d was accomplished following the previously described procedure (Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078) consisting in the reaction of l-menthyl (S)-p-toluenesulfinate (Mioskowsky, C.; Solladié, G. Tetrahedron 1980, 36, 227. Solladié, G. Synthesis 1981, 185) and the corresponding 1-alkynyl-magnesium bromide in toluene. In our hands, the reaction temperature had to be increased from -20 °C, as described, to 20 °C in order to get good yields.
32. The synthesis of optically pure 1-alkynyl p-tolyl sulfoxides 2a-d was accomplished following the previously described procedure (Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078) consisting in the reaction of l-menthyl (S)-p-toluenesulfinate (Mioskowsky, C.; Solladié, G. Tetrahedron 1980, 36, 227. Solladié, G. Synthesis 1981, 185) and the corresponding 1-alkynyl-magnesium bromide in toluene. In our hands, the reaction temperature had to be increased from -20 °C, as described, to 20 °C in order to get good yields.
33. (a) García Ruano, J. L.; Martín Castro, A. M.; Rodríguez, J. H. Tetrahedron Lett. 1991, 32, 3195.
34. (b) García Ruano, J. L.; Martín Castro, A. M.; Rodríguez, J. H. J. Org. Chem. 1992, 57, 7235.
35. (c) Escribano, A.; García Ruano, J. L.; Martín Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567.
36. 2AlCN (unpublished results) in those cases requiring long reaction times. The course of these reactions is not clear.
37. 1 we postulate the formation of B, the hydrolysis of which and further deprotonation explain the formation of 5c.
38. At low temperature (-78 °C), thioester 5c was detected only after long reaction times.
39. A decrease in the reaction temperature hinders the transformation of substrate 2b and favors the predominance of undesired products.
40. Kunz, H.; Sager, W.; Pfrengle, W.; Schanzenbach, D. Tetrahedron Lett. 1988, 29, 4397.
41. Lower reactivity and sluggish reactions containing so far unidentified decomposition products were the general characteristics of these reactions. Under the best conditions, compound 2a yielded la (60% estimated yield) at 0 °C after 72 h, whereas 1b was obtained from 2b (-78 °C, 46 h, 42% estimated yield by NMR), and le from 2c (0 °C, 21 h, 62% estimated yield).
42. To check this assumption, we carried out the cycloaddition of 1a in solvents of higher polarity, thus favoring the most polar s-cis conformations. The obtained results indicate the formation of a mixture containing four adducts, the proportion of the two new adducts being higher with the increase in the solvent polarity (Table 3, entries 9 and 10).
43. Guessous, A.; Rouessac, F.; Maignan, C. Bull. Soc. Chim. Fr. 1986, 837.
44. Brimble, M. A.; Davis, B. R. Tetrahedron 1985, 41, 4965.
45. (a) Arai, Y.; Hyashi, Y.; Matatoshi, Y.; Takayama, H.; Koizumi, T. Chem. Lett. 1987, 185.
46. (b) Arai, Y.; Hayashi, Y.; Matatoshi, Y.; Takayama, H.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1988, 3133.
47. (c) Takayama, H.; Iyobe, A.; Koizumi, T. Chem. Pharm. Bull. 1987, 35, 433.
48. (d) Takahashi, T.; Iyobe, A.; Arai, Y.; Koizumi, T. Synthesis 1989, 189.
49. (e) Takahashi, T.; Katsubo, H.; Zyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065.
50. (f) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137.
51. (g) Takayama, H.; Hayashi, K.; Koizumi, T. Tetrahedron Lett. 1986, 27, 5509.
52. It had been unsuccessfully used with sulfinylacrylates (ref 10).
53. García Ruano, J. L.; Martín Castro, A. M.; Rodríguez Ramos, J. H. Tetrahedron Lett. 1996, 37, 4569.
54. García Ruano, J. L.; Martín Castro, A. M.; Rodríguez J. H. Rubio Flamarique, A. C. Tetrahedron: Asymmetry 1997, 8, 3503.
55. These conditions were not successful for 1a and 1d, which yielded mixtures containing 8a and 8d in minor proportion. The structure of the major compounds obtained in these reactions is currently under investigation. Under
56. Hall, J. H.; Gisler, M. J. Org. Chem. 1976, 41 3769. Under these conditions, sulfur configuration should not be affected.
57. In this reaction compound 11 was also recovered (see Experimental Section). It results from epimerization at C-α of the sulfinyl group under basic reaction conditions.
58. We are currently investigating the mechanistic proposal depicted in Schemed to explain the inversion of the herein described Configuration, studying the scope of these hydrolysis reactions for other β-sulfinyl nitriles and related substrates, and searching the proper experimental conditions to get the complete invention of the sulfoxides in acidic medium. The results of this study will be published in due course.
59. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemical, 2nd ed.; Pergamon Press: New York, 1980.
60. Vogel A. I. Practical Organic Chemistry, 5th ed., Longman Scientific and Technical: London, 1989; p 1122.
61. 22SO: C, 81-04; H, 5.98; S, 8.51. Found: C, 80.51; H, 5.75; S, 8.47.