An efficient procedure for preparing γ-hydroxy α,β-unsaturated sulfones

European Journal of Organic Chemistry

Volumn , Issue 7, 1999, Pages 1545-1550

  Zoller, Thomas ^a   Uguen, Daniel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Sulfones; Takai Hiyama Nozaki Kishi coupling; Ionone

Indexed keywords

1 [1 METHYL 1,3 BUTADIEN 1 YL] 2 [3 OXO 4 TOSYL 3 BUTEN 1 YL]CYCLOHEXANE; 2 [3 HYDROXY 4 TOSYL 3 BUTEN 1 YL] 1 [1 METHYL 1,3 BUTADIEN 1 YL]CYCLOHEXANE; ALDEHYDE; BETA IONONE; CHROMIUM; SULFONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032804421     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199907)1999:7<1545::aid-ejoc1545>3.0.co;2-n     Document Type: Article

References (72)

1. T. Zoller, D. Uguen, A. De Cian, J. Fischer, Tetrahedron Lett. 1997, 38, 3409-3412.
2. From sulfinylmethyl arylsulfones: [2a] E. Dominguez, J. C. Carretero, Tetrahedron Lett. 1990, 31, 2487-2490.
3. [2b] B. M. Trost, T. A. Grese, J. Org. Chem. 1991, 56, 3189-3192.
4. [2c] R. F. W. Jackson, S. P. Standen, W. Clegg, J. Chem. Soc., Perkin Trans. II 1995, 149-156, and quoted references therein.
5. From allylic sulfones: [3a] G. S. Ananda, P. J. Crenins, R. J. Stoodley, J. Chem. Soc., Chem. Commun. 1987, 882 and quoted references therein.
6. [3b] K. Ogura, N. Shibuya, H. Iida, Tetrahedron Lett. 1981, 22, 1519-1522.
7. [3c] K. Ogura, N. Shibuya, K. Takahashi, H. Iida, Bull. Chem. Soc. Jpn. 1984, 57, 1092-1096.
8. From β,γ-epoxysulfones: [4a] A. D. Westwell, M. Thornton-Pett, C. M. Rayner, J. Chem. Soc., Perkin Trans. II 1995, 847-859.
9. [4b] D. K. Hutchinson, P. L. Fuchs, J. Am. Chem. Soc. 1985, 107, 6137-6138.
10. [4c] J. C. Sadler, R. E. Hutchinson, P. L. Fuchs, J. Am. Chem. Soc. 1981, 103, 2110-2112.
11. [4d] J. C. Sadler, P. L. Fuchs, J. Am. Chem. Soc. 1981, 103, 2112-2114.
12. [4e] J. E. Bäckvall, S. K. Juntunen, J. Org. Chem. 1988, 53, 2398-2400.
13. [4f] T. Sakakibara, I. Takai, A. Yamamoto, H. Iizuka, K. Hirasawa, Y. Ishido, Tetrahedron Lett. 1990, 31, 3749-3752.
14. [4g] Y. Pan, S. A. Hardinger, P. L. Fuchs, Synth. Commun. 1989, 19, 403-416.
15. [4h] S. A. Hardinger, P. L. Fuchs, J. Org. Chem. 1987, 52, 2739-2749.
16. [4i] O. Arjona, R. F. de la Pradilla, A. Mallo, J. Plumet, A. Viso, Tetrahedron Lett. 1990, 31, 1475-1478.
17. [4j] J. Adrio, J. C. Carretero, R. G. Arrayàs, Synlett 1996, 640-642.
18. [4k] A. K. Maiti, P. Bhattacharyya, Tetrahedron 1994, 50, 10483-10490.
19. [4l] P. Bhattacharyya, G. K. Biswas, Synth. Commun. 1991, 21, 569-573.
20. [4m] J. K. Crandall, C. Pradat, J. Org. Chem. 1985, 50. 1327-1329.
21. [4n] C. C. J. Culvenor, W. Davies, W. E. Savige, J. Chem. Soc. 1949, 1419-1423.
22. [4o] A. M. Bernard, M. T. Cocco, C. Congiu, G. L. Franzone, P. P. Piras, Synthesis 1996, 361-366.
23. [4p] B. M. Trost, M. G. Organ, G. A. O'Doherty, J. Am. Chem. Soc. 1995, 117, 9662-9670.
24. [4q] S. W. Lee, P. L. Fuchs, Tetrahedron Lett. 1991, 32, 2861-2864.
25. From 1-arylsulfonyl propargylic alcohols: I. Ryu, N. Kusumoto, A. Ogawa, N. Kambe, N. Sonoda, Organometallics 1989, 8, 2279-2281.
26. From 2-hetero-substituted 3-hydroxyalkylsulfones and O-derivatives: [6a] S.-K. Kang, J. Chem. Soc., Perkin Trans. II 1992, 405-406.
27. [6b] D. Quiu, R. R. Schmidt, Synthesis 1990, 875-877.
28. [6c] N. J. Barnes, A. H. Davidson, L. R. Hughes, G. Procter, J. Chem. Soc., Chem. Commun. 1985, 1292-1294.
29. [6d] S. G. Pyne, D. C. Spellmeyer, S. Chen, P. L. Fuchs, J. Am. Chem. Soc. 1982, 104, 5728-5740.
30. [6e] J. F. Cassidy, J. M. Williams, Tetrahedron Lett. 1986, 27, 4355-4538.
31. [6f] D. K. Hutchinson, S. A. Hardinger, P. L. Fuchs, Tetrahedron Lett. 1986, 27, 1429-1432.
32. [6g] D. K. Hutchinson, P. L. Fuchs, Tetrahedron Lett. 1986, 27, 1425-1428.
33. [6h] C. Nàjera, A. Pérez-Pinar, J. M. Sansano, Tetrahedron 1991, 47, 6337-6352.
34. [6i] C. Nàjera, B. Baldò, M. Yus, J. Chem. Soc. Perkin Trans. II 1988, 1029-1032.
35. [6j] S. Sengupta, D. Sen Sarma, S. Mondal, Tetrahedron: Asymmetry 1998, 2311-2316.
36. From allylic bis(sulfones): T. Cuvigny, K. Du Penhoat, M. Julia, Rec. Trav. Chim. Pays-Bas 1986, 105, 409-421.
37. From vinyl arylsulfones: [8a] D. H. R. Barton, S. D. Gero, B. Quiclet-Sire, M. Samadi, Tetrahedron: Asymmetry 1994, 5, 2123 -2136.
38. [8b] D. H. R. Barton, A. Gateau-Olesker, S. D. Gero, B. Lacher, C. Tachdjian, S. Z. Zard, Tetrahedron 1993, 49, 4589-4602.
39. From α-oxygenated aldehydes: S. F. Wnuk, N. K. Dalley, M. Robins, Can. J. Chem. 1991, 69, 2104-2111.
40. [10a] E. Dominguez, J. C. Carretero, Tetrahedron 1994, 50, 7557-7566.
41. [10b] J. C. Carretero, E. Dominguez, J. Org. Chem. 1993, 58, 1596-1600.
42. [10c] F. M. Leon, J. C. Carretero, Tetrahedron Lett. 1991, 32, 5405-5408.
43. [10d] M. Isobe, Y. Ichikawa, Y. Funabashi, S. Mio, T. Goto, Tetrahedron 1986, 42, 2863-2872.
44. [10e] M. Kitamura, M. Isobe, Y. Ichikawa, T. Goto, J. Am. Chem. Soc. 1984, 106, 3252-3257.
45. [10f] M. Isobe, Y. Ichikawa, H. Masaki, T. Goto, Tetrahedron Lett. 1984, 25, 3607-3610.
46. [10g] P. L. Fuchs, T. F. Braish, Chem. Rev. 1986, 86, 903-917.
47. [10h] J. Adrio, J. C. Carretero, R. G. Arrayàs, Synlett 1996, 640-642.
48. [10i] R. Noyori, M. Suzuki, Angew. Chem. Int. Ed. Engl. 1984, 23, 847-876, and references cited therein.
49. [10j] B. M. Trost, P. Seoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487-7500.
50. [10k] I. Alonso, J. L. Garrido, V. Magro, C. Pedregal, J. Org. Chem. 1997, 62, 5682-5683.
51. [10l] J. C. Carretero, E. Dominguez, J. Org. Chem. 1992, 57, 3867-3873.
52. [10m] K. Ogura, K.-I. Ogu, T. Ayabe, J.-I. Sonehara, M. Akazome, Tetrahedron Lett. 1997, 38, 5173-5176.
53. [11a] C. Mercier, Doctorate dissertation, Paris VI, 1984.
54. [11b] M. Julia, C. Lefebvre, Tetrahedron Lett. 1984, 25, 189-192.
55. [11c] C. Mercier, M. Julia, D. Uguen, unpublished results. For instance, (Z)-3-methyl-1-(p-tolylthio)-1-buten-3-ol, which is formed exclusively upon treatment of 3-methyl-1-butyne-3-ol with p-thiocresol in basic, protic media and under strictly anaerobic conditions, was shown to give, besides a small amount of its regioisomer [i.e. 3-methyl-2-(p-tolylthio)-1-buten-3-ol], the stereomeric (E)-hydroxysulfide upon treatment with traces of p-thiocresol and either AIBN or oxygen, in dichloromethane.
56. T. Zoller, D. Uguen, Tetrahedron Lett. 1998, 39, 8089-8092.
57. [13a] K. Takai, K. Kimura, T. Kuroda, T. Hiyama, H. Nozaki, Tetrahedron Lett. 1983, 24, 5281-5284.
58. [13b] K. Kishi, Pure Appl. Chem. 1992, 64, 343-350, and references therein.
59. [13c] For a review, see: P. Cintas, Synthesis 1992, 248-257; L. A. Luger, A. Wessjohann, G. Scheid Synthesis, 1999, 1-36.
60. [13c] For a review, see: P. Cintas, Synthesis 1992, 248-257; L. A. Luger, A. Wessjohann, G. Scheid Synthesis, 1999, 1-36.
61. [14a] V. Farina, S. I. Hauck, J. Org. Chem. 1991, 56, 4317-4319.
62. [14b] C. J. Rao, P. Knochel, J. Org. Chem. 1991, 56, 4593-4596.
63. [14c] M. Ochiai, T. Ukita, E. Fujita, Tetrahedron Lett. 1983, 24, 4025-4028.
64. [14d] J. S. Xiang, A. Mahadevan, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 4284-4290.
65. [14e] W. E. Truce, A. W. Borel, P. J. Marek, J. Org. Chem. 1976, 41, 401-402.
66. G. Oddon, D. Uguen, Tetrahedron Lett. 1998, 39, 1157-1160.
67. [16a] J. R. parikh, W. von E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507.
68. [16b] K. Nakagawa, R. Konaka, T. Nakata, J. Org. Chem. 1962, 27, 1597-1601.
69. [16c] D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
70. [16d] S. M. Rubistein, R. M. Williams, J. Org. Chem. 1995, 60, 7215-7223.
71. Due to the sensitivity of the aldehyde 1, which decomposes within a few days on standing at room temperature, execution of the 1-4a condensation by us did not proceed satisfactorily under these conditions.
72. th, 1998.