Enantioselective protonation of the lithium transient enolate of 2-methyltetralone with 2-sulfinyl alcohols

European Journal of Organic Chemistry

Volumn , Issue 8, 2005, Pages 1561-1567

  Gil, Jesús ^a   Medio Simon, Mercedes ^a   Mancha, Gisela ^a   Asensio, Gregorio ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

2 methyltetralone; 2 sulfinyl alcohols; Enantioselective protonation; Lithium enolates

Indexed keywords

EID: 18144429900     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400812     Document Type: Article

References (66)

1. Reviews a) J. Eames, N. Weerasooriya, Tetrahedron: Asymmetry 2001, 12, 1-24;
2. b) C. Fehr, Angew. Chem. Int. Ed. Engl. 1996, 35, 2566-2587;
3. c) A. Yanagisawa, H. Yamamoto, In Comprehensive Asymmetric Catalysis, vol. II (Eds.: E. N. Jacobsen, A. Platz, H. Yamamoto), Springer, Berlin, 1999, 2566.
4. a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726-3748;
5. b) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
6. E. Vedejs, N. Lee, S. T. Sakata, J. Am. Chem. Soc. 1994, 116, 2175-2176.
7. a) C. Fehr, N. Chaptal-Gradoz, J. Galindo, Chem. Eur. J. 2002, 8, 853-858;
8. b) C. Fehr, J. Galindo, J. Am. Chem. Soc. 1988, 110, 6909-6911;
9. c) C. Fehr, O. Guntern, Helv. Chim. Acta 1992, 75, 1023-1028.
10. J.-C. Raymond, G. K. Jahangiri, C. Stoudt, R. A. Lerner, J. Am. Chem. Soc. 1993, 115, 3909-3917.
11. Reports after reviews a) D. R. Carbery, T. J. Donohoe, Chem. Commun. 2004, 722-723;
12. b) L. Navarre, S. Darses, J.-P. Genet, Angew. Chem. Int. Ed. 2004, 43, 719-723;
13. c) Y. Hamashima, H. Somei, Y. Shimura, T. Tamura, M. Sodeoka, Org. Lett. 2004, 6, 1861-1864;
14. d) B. M. Kim, W. Kim, K. Y. Im, J. K. Park, J. Org. Chem. 2004, 69, 5104-5107;
15. e) C. Fehr, J. Galindo, I. Farris, A. Cuenca, Helv. Chim. Acta 2004, 87, 1737-1747;
16. f) O. Munoz-Muniz, E. Juaristi, Tetrahedron Lett. 2003, 44, 2023-2026;
17. g) K. Futasugi, A. Yanagisawa, H. Yamamoto, Chem. Commun. 2003, 566-567;
18. h) T. Bach, B. Grosch, T. Strassner, E. Herdtweck, J. Org. Chem. 2003, 68, 1107-1116;
19. i) M. Clericuzio, I. Degani, S. Dughera, R. Fochi, Tetrahedron: Asymmetry 2003, 14, 119-125;
20. j) O. Roy, A. Riahi, F. Henin, J. Muzart, Eur. J. Org. Chem. 2002, 3986-3994;
21. k) A. Yanagisawa, Y. Matsuzaki, H. Yamamoto, Synlett 2001, 1855-1858.
22. Reports after reviews a) Y. Ohtsuka, T. Ikeno, T. Yamamada, Tetrahedron: Asymmetry 2003, 14, 967-970;
23. b) K. Flinois, Y. Yuan, C. Bastide, A. Harrison-Marchand, J. Maddaluno, Tetrahedron 2002, 58, 4707-4716.
24. a) A. Yanagisawa, T. Kuribayashi, T. Kikuchi, H. Yamamoto, Angew. Chem. Int. Ed. Engl. 1994, 33, 107-109;
25. b) A. Yanagisawa, T. Kikuchi, T. Kuribayashi, H. Yamamoto, Tetrahedron 1998, 54, 10253-10264;
26. c) A. Yanagisawa, T. Kikuchi, T. Kuribayashi, H. Yamamoto, Synlett 1998, 174-176;
27. d) Y. Nakamura, S. Takeuchi, Y. Ohgo, M. Yamaoka, A. Yoshida, K. Mikami, Tetrahedron 1999, 55, 4595-4620;
28. e) G. Asensio, A. Cuenca, N. Rodriguez, M. Medio-Simon, Tetrahedron: Asymmetry 2003, 14, 3851-3855;
29. f) H. Kosugi, K. Hoshino, H. Uga, Tetrahedron Lett. 1997, 38, 6861-6864.
30. J. Ahman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918-1919.
31. 〈lit10 〉a) K. Ishihara, D. Nakashima, Y. Hiraiwa, H. Yamamoto. J. Am. Chem. Soc. 2003, 125, 24-25;
32. b) K. Ishihara, H. Nakamura, S. Nakamura, H. Yamamoto, J. Org. Chem. 1998, 63, 6444-6445;
33. c) S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc 2000, 122, 8120-8130.
34. Catalytic internal quench: a) C. Fehr, I. Stempf, J. Galindo, Angew. Chem. Int. Ed. Engl. 1993, 32, 1044-1046;
35. b) C. Fehr, J. Galindo, Angew. Chem. Int. Ed. Engl. 1994, 33, 1888-1889;
36. c) C. Fehr, J. Galindo, Helv. Chim. Acta 1995, 78, 539-552;
37. d) E. Vedejs, A. W. Kruger, J. Org. Chem. 1998, 63, 2792-2793;
38. e) E. Vedejs, A. W. Kruger, N. Lee, S. T. Sakata, M. Stec, E. Suna, J. Am. Chem. Soc. 2000, 122, 4602-4607;
39. f) A. Yanagisawa, T. Watanabe, T. Kikuchi, H. Yamamoto, J. Org. Chem. 2000, 65, 2979-2983;
40. g) A. Yanagisawa, T. Watanabe, T. Kikuchi, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8120-8130;
41. h) A. Yanagisawa, T. Watanabe, T. Kikuchi, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 12854-12855;
42. i) T. Watanabe, T. Kuribayashi, H. Yamamoto, Synlett 1995, 372-374;
43. j) J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381-389;
44. k) Y. Nakamura, S. Takeuchi, A. Ohira, Y. Ohgo, Tetrahedron Lett. 1996, 37, 2805-2808;
45. m) S. Takeuchi, Y. Nakamura, Y. Ohgo, D. P. Curran, Tetrahedron Lett. 1998, 39, 8691-8694.
46. Catalytic external quench: a) K. Nishimura, M. Ono, Y. Nagaoka, K. Tomioka, Angew. Chem. Int. Ed. 2001, 40, 440-442;
47. b) Y. Yamashita, Y. Emura, K. Odashima, K. Koga, Tetrahedron Lett. 2000, 41, 209-213;
48. c) E. Emori, A. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 4043-4044;
49. d) M. Sugiura, T. Nakai. Angew. Chem. Int. Ed. Engl. 1997, 36, 2366-2368;
50. e) P. Riviere, K. Koga, Tetrahedron Lett. 1997, 38, 7589-7592.
51. E. Vedejs, A. W. Kruger, E. Suna, J. Org. Chem. 1999, 64, 7863-7870.
52. a) G. Asensio, P. A. Aleman, L. R. Domingo, M. Medio-Simon, Tetrahedron Lett 1998, 39, 3277-3280;
53. b) G. Asensio, P. A. Aleman, J. Gil, L. R. Domingo, M. Medio-Simon, J. Org. Chem. 1998, 63, 9342-9347;
54. c) G. Asensio, P. A. Aleman, A. Cuenca, J. Gil, M. Medio-Simon, Tetrahedron: Asymmetry 1998, 9, 4073-4078;
55. d) G. Asentio, A. Cuenca, P. Gavina, M. Medio-Simon, Tetrahedron Lett. 1999, 40, 3939-3940;
56. e) G. Asensio, P. Gavina, A. Cuenca, M. C. Ramirez de Arellano, L. R. Domingo, M. Medio-Simon, Tetrahedron: Asymmetry 2000, 11, 3481-3493.
57. G. Asensio, J. Gil, P. A. Aleman, M. Medio-Simon, Tetrahedron: Asymmetry 2001, 12, 1359-1362.
58. a) H. O. House, L. J. Czuba, M. Gall, H. D. Olmstead, J. Org. Chem. 1969, 34, 2324-2336;
59. b) H. O. House, M. Gall, H. D. Olmstead, J. Org. Chem. 1971, 36, 2361-2371.
60. a) P. Duhamel, D. Cahard, Y. Quesnel, J.-M. Poirier, J. Org. Chem. 1996, 61, 2232-2235;
61. b) D. Cahard, P. Duhamel, Eur. J. Org. Chem. 2001, 1023-1031.
62. P. Strazzoli, G. Verardo, A. G. Giumarini, J, Org. Chem. 1988, 53, 3321-3325.
63. a) A. Abbotto, A. Streitwieser, P. von Rague Schleyer. J. Am. Chem. Soc. 1997, 119, 11255-11268;
64. b) D. Seebach, Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654.
65. F. Cavelier, S. Gomez, R. Jacquier, J. Verducci, Tetrahedron Lett. 1994, 35, 2891-2894.
66. F. Cazeau, F. Duboidin, F. Moulines, O. Babot, J. Donouges, Tetrahedron 1987, 43, 2075-2088.