3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6404-6416

  Alonso, Diego A ^a   Fuensanta, Mónica ^a   Nájera, Carmen ^a   Varea, Montserrat ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ALKYLATION; CARBONYLATION; COMPLEXATION; OLEFINS; OXIDATION; REACTION KINETICS; STEREOCHEMISTRY;

CARBONYL COMPOUNDS; OLEFINATION REACTION; STREOSELECTIVITY; SULFONES;

KETONES;

1 PHENYL 1H TETRAZOL 5 YL SULFONE; 1 TERT BUTYL 1H TETRAZOL 5 YL SULFONE; 3,5 BIS(TRIFLUOROMETHYL)PHENYL SULFONE DERIVATIVE; BENZOTHIAZOL 2 YL SULFONE; POTASSIUM HYDROXIDE; RESVERATROL; STILBENE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; OLEFINATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 23044453113     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050852n     Document Type: Article

References (84)

1. (a) Wittig, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44-68.
2. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
3. (a) Horner, L.; Hoffmann, H.; Wipel, H. C.; Klahre, G. Chem. Ber. 1959, 92, 2499-2505.
4. (b) Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 241-270.
5. (a) Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733-1738.
6. (b) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-89.
7. (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780-784.
8. (b) van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195-200.
9. Johnson, C. R.; Shanklin, J. R.; Kirchhoff, R. A. J. Am. Chem. Soc. 1973, 95, 6462-6463.
10. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836.
11. For a review about desulfonylation reactions, see: Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547-10658.
12. Prilezhaeva, E. N. Russ. Chem. Rev. 2000, 69, 367-408.
13. (a) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32, 1175-1178.
14. (b) Baudin, J. B.; Hareau, G.; Julia, S. A.; Lorne, R.; Ruel, O. Bull. Soc. Chim. Fr. 1993, 130, 336-357.
15. (c) Baudin, J. B.; Hareau, G.; Julia, S. A.; Lorne, R.; Ruel, O. Bull. Soc. Chim. Fr. 1993, 130, 856-878.
16. For a recent review, see: Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
17. Bellingham, R.; Jarowicki, K; Kocienski, P.; Martin, V. Synthesis 1996, 285-296.
18. Kocienski, P. Synthesis 1996, 652-666.
19. Lee, E.; Song, H. Y.; Kang, J. W.; Kim, D.-S.; Jung, C.-K.; Joo, J. M. J. Am. Chem. Soc. 2004, 124, 384-385.
20. (a) Kang, S. H.; Kang, S. Y.; Kim, C. M.; Choi, H.-W.; Jun, H.-S.; Lee, B. M.; Park, C. M.; Jeong, J. W. Angew. Chem., Int. Ed. 2003, 42, 4779-4782.
21. (b) Kang, S. H.; Kang, S. Y.; Choi, H.-W.; Kim, C. M.; Jun, H.-S.; Youn, J.-H. Synthesis 2004, 1102-1114.
22. (a) Lafontaine, J. A.; Provencal, D. P.; Gardelli, C.; Leahy, J. W. Tetrahedron Lett. 1999, 40, 4145-4148.
23. (b) Lafontaine, J. A.; Provencal, D. P.; Gardelli, C.; Leahy, J. W. J. Org. Chem. 2003, 68, 4215-4234.
24. (c) Jiang, Y.; Hong, J.; Burke, S. D. Org. Lett. 2004, 6, 1445-1448.
25. (a) Pattenden, G.; Plowright, A. T.; Tornos, J. A.; Ye, T. Tetrahedron Lett. 1998, 40, 6099-6102.
26. (b) Pattenden, G.; Gonzalez, M. A.; Little, P. B.; Millan, D. S.; Plowright, A. T.; Tornos, J. A.; Ye, T. Org. Biomol. Chem. 2003, l, 4173-4208.
27. (c) Pattenden, G.; Gonzalez, M. A. Angew. Chem., Int. Ed. 2003, 42, 1255-1258.
28. (a) Evans, D. A.; Cee, V. J.; Smith, T. E.; Fitch, D. M.; Cho, P. S. Angew. Chem., Int. Ed. 2000, 39, 2533-2536.
29. (b) Li, D. R.; Tu, Y. Q.; Lin, G.-Q.; Zhou, W.-S. Tetrahedron Lett. 2003, 44, 8729-8732.
30. (c) Li, D. R.; Sun, C. Y.; Su, C.; Lin, G.-Q.; Zhou, W.-S. Org. Lett. 2004, 6, 4261-4264.
31. (a) Furuichi, N.; Hara, H.; Osaki, T.; Nakano, M.; Mori, H.; Ratsumura, S. J. Org. Chem. 2004, 69, 7949-7959.
32. (b) Vaz, B.; Alvarez, R.; Bruckner, R.; de Lera, A. R. Org. Lett. 2005, 7, 545-548.
33. Harrowven, D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, 1221-1222.
34. (a) Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 5149-5153.
35. (b) Corrigendum: Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 6619.
36. Blakemore, P. R.; Cole, W. J.; Rocienski, P. J.; Morley, A. Synlett 1998, 26-28.
37. Rocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365-366.
38. For the latest applications of PT sulfones in total synthesis, see: (a) Cramer, N.; Laschat, S.; Baro, A.; Schwalbe, H.; Richter, C. Angew. Chem., Int. Ed. 2005, 44, 820-822.
39. (b) Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2005,127, 1628-1629.
40. (c) Jasper, C.; Wittenberg, R.; Quitschalle, M.; Jakupovic, J.; Kirschning, A. Org. Lett. 2005, 7, 479-482.
41. Truce, W. E.; Kreider, E. M.; Brand, W. W. Org. React. 1970, 18, 99-215.
42. (a) Alonso, D. A.; Nájera, C.; Varea, M. Tetrahedron Lett. 2001, 42, 8845-8848.
43. (b) Alonso, D. A.; Nájera, C.; Varea, M. Helv. Chim. Acta 2003, 55, 4287-4305.
44. Alonso, D. A.; Nájera, C.; Varea, M. Synthesis 2003, 277-287.
45. (a) Alonso, D. A.; Nájera, C.; Varea, M. Tetrahedron Lett. 2004, 45, 573-577.
46. (b) Alonso, D. A.; Fuensanta, M.; Nájera, C.; Varea, M. Phosphorus, Sulfur, and Silicon Relat. Elem. 2005, 180, 1119-1131.
47. Alonso, D. A.; Nájera, C. 3,5-Bis(trifluoromethyl)benzenethiol. In Encyclopedia of Reagents for Organic Synthesis; Wiley & Sons, http:// www.mrw.interscience.wiley.com/eros, in press.
48. This is a simple, green, and general method for the oxidation of sulfides to sulfones: Alonso, D. A.; Nájera, C.; Varea, M. Tetrahedron Lett. 2002, 43, 3459-3461.
49. (a) Schwesinger, R. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995; Vol. 6, p 4110.
50. (b) Schwesinger, R.; Schlemper, H.; Hasenfratz, C.; Willaredt, J.; Dambacher, T.; Breuer, T.; Ottaway, C.; Fletschinger, M.; Boele, J.; Fritz, H.; Putzas, D.; Rotter, H. W.; Bordwell, F. G.; Satish, A. V.; Ji, G.-Z.; Peters, E. M.; Peters, K.; von Schnering, H. G.; Walz, L. Liebigs Ann. Chem. 1996, 1055-1081.
51. (c) Seebach, D.; Beck, A. K.; Studer, A. Modern Synthetic Methods 1995, 7, 1-178.
52. Uguen has proposed the formation of carbene species from benzyl sulfone carbanions to explain the observed formation of stilbenes in very low yields in the reduction with sodium amalgam of benzyl sulfones: Jolivet, B.; Uguen, D. Tetrahedron Lett. 2002, 43, 7907-7911.
53. Julia, M.; Le Thuillier, G.; Rolando, Ch.; Saussine, L. Tetrahedron Lett. 1982, 23, 2453-2456.
54. (a) Julia, M.; Verpeaux, J.-N. Tetrahedron Lett. 1982, 23, 2457-2460.
55. (b) Gai, Y.; Julia, M.; Verpeaux, J.-N. Bull. Soc. Chim. Fr. 1996, 733, 805-816.
56. Engman, L. J. Org. Chem. 1984, 49, 3559-3563.
57. Jin, L.; Julia, M.; Verpeaux, J. N. Synlett 1994, 215-216.
58. Heathcock has noticed the oxygen-catalyzed oxidative coupling of two alkyl sulfone anions to give an alkene after the reductive elimination of a bis sulfone intermediate: Heathcock, C. H.; Finkelstein, B. L.; Jarvi, E. T.; Radel, P. A.; Hadley, C. R. J. Org. Chem. 1988, 53, 1922-1942.
59. Benzyl sulfones have been successfully deprotonated by phosphazene base P4-t-Bu in the diastereoselective aldol reaction with aldehydes: (a) Solladié-Cavallo, A.; Roche, D.; Fischer, J.; De Chian, A. J. Org. Chem. 1996, 61, 2690-2694.
60. (b) Costa, A.; Nájera, C.; Sansano, J. M. J. Org. Chem. 2002, 67, 5216-5225.
61. (a) Siemann, E. H.; Creasy, L. L. Am. J. Enol. Vitic. 1992, 43, 49-52.
62. (b) Soleas, G. J.; Diamandis, E. P.; Goldberg, D. M. Clin. Biochem. 1997, 62, 4821-4826.
63. (c) Jang, M.; Cai, L.; Udenai, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218-220.
64. (d) Orsini, F.; Pelizzoni, F.; Verotta, L.; Aburjai, T.; Rogers, C. B. J. Nat. Prod. 1997, 60, 1082-1087.
65. (e) Fremont, L. Life Sci. 2000, 66, 663-673.
66. (f) Gusman, J.; Malonne, H.; Atassi, G. Carcinogenesis 2001, 22, 1111-1117.
67. (g) Howitz, K. T.; Bitterman, K. J.; Cohen, H. Y.; Lamming, D. W.; Lavu, S.; Wood, J. G.; Zipkin, R. E.; Chung, P.; Kisielewski, A.; Zhang, L. L.; Scherer, B.; Sinclair, D. A. Nature 2003, 425, 191-196.
68. (h) Lamming, D. W.; Wood, J. G.; Sinclair, D. A. Mol. Microbiol. 2004, 53, 1003-1009.
69. For a very recent synthesis of methoxylated stilbenoids employing Heck chemistry in our group, see: Botella, L.; Nájera, C. Tetrahedron 2004, 60, 5563-5570.
70. (a) Pettit, G. R.; Grealish, M. P.; Jung, M. K.; Hamel, E.; Pettit, R. K.; Chapuis, J.-C.; Schmidt, J. M. J. Med. Chem. 2002, 45, 2534-2542.
71. (b) Lion, C. J.; Matthews, C. S.; Stevens, F. G.; Westwell, A. D. J. Med. Chem. 2005, 48, 1292-1295.
72. For a discussion about the nature of P4-t-Bu enolates, see: Fruchart, J.-S.; Gras-Masse, H.; Melnyk, O. Tetrahedron Lett. 2001, 42, 9153-9155.
73. Kim, S.; Ko, H.; Park, J. E.; Jung, S.; Lee, S. K.; Chun, Y.-J. J. Med. Chem. 2002, 45, 160-164.
74. Kelly, S. E. Alkene Synthesis. In Comprehensive Organic Synthesis; Trost, B. M. Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 729.
75. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.
76. Pine, S. H.; Zahier, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270-3272.
77. (a) Mo-catalyzed: Lu, X. Y.; Fang, H.; Ni, Z. J. J. Organomet. Chem. 1989, 373, 77-84.
78. (b) Re-catalyzed: Zhang, X. Y.; Chen, P. Chem.-Eur. J. 2003, 9, 1852-1859 and references therein,
79. (c) Fe-catalyzed: Aggarwal, V. K.; Fulton, J. R.; Sheldon, C. G.; de Vicente, J. J. Am. Chem. Soc. 2003, 125, 6034-6035 and references therein,
80. (d) Ru-catalyzed: Chen, Y.; Huang, L.; Ranade, M. A.; Zhang, X. P. J. Org. Chem. 2003, 68, 3714-3717 and references therein,
81. (e) Rh-catalyzed: Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328 and references therein.
82. 2Me, see refs 9a,c and Gueyrard, D.; Haddoub, R.; Salem, A.; Bavar, N. S.; Goekjian, P. G. Synlett 2005, 520-522.
83. Van der Wiel, B. C.; Williams, R. M.; van Walree, C. A. Org. Biomol. Chem. 2004, 2, 3432-3433.
84. All attempts to isolate or detect β-hydroxy sulfones 15 from the reaction between sulfone 7a and benzaldehyde under different conditions were unfruitful due to the fast Smiles rearrangement and elimination of SÛ2 that these systems suffer from.