Highly-functionalised difluorinated cyclohexane polyols via the Diels-Alder reaction: Regiochemical control via the phenylsulfonyl group

Organic and Biomolecular Chemistry

Volumn 3, Issue 18, 2005, Pages 3297-3310

  Crowley, Patrick J ^a   Fawcett, John ^b   Griffith, Gerry A ^b   Moralee, Andrew C ^b   Percy, Jonathan M ^b   Salafia, Vittoria ^b  

^a JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; FURAN RESINS; OXIDATION;

DIFLUORINATED DIENOPHILE; OXABICYCLIC PRODUCTS; POLYOLS;

ALCOHOLS;

BETULACEAE;

EID: 26444470483     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b507131c     Document Type: Article

References (92)

1. P. Vogel, J. Cossy, J. Plumet and O. Arjona, Tetrahedron, 1999, 55, 13521-13642.
2. B. V. L. Potter and D. Lampe, Angew. Chem., Int. Ed. Engl., 1995, 34, 1933-1972.
3. M. S. Gultekin, M. Celik and M. Balci, Curr. Org. Chem., 2004, 8, 1159-1186.
4. K. Hiroya and K. Ogasawara, Chem. Commun., 1999, 8, 2197-2198;
5. O. Arjona, F. Iradier, R. M. Manas and J. Plumet, Tetrahedron Lett., 1998, 39, 8335-8336.
6. D. J. A. Schedler and D. C. Baker, Carbohydr. Res., 2004, 339, 1585-1595.
7. R. P. Singh and J. M. Shreeve, Synthesis, 2002, 339, 2561-2578.
8. For a recent large scale application of this approach, see: T. Mase, I. N. Houpis, A. Akao, I. Dorziotis, K. Emerson, T. Hoang, T. Iida, T. Itoh, K. Kamei, S. Kato, Y. Kato, M. Kawasaki, F. R. Lang, J. M. Lee, J. Lynch, P. Maligres, A. Molina, T. Nemoto, S. Okada, R. Reamer, J. Z. Song, D. Tschaen, T. Wada, D. Zewge, R. P. Volante, P. J. Reider and K. Tomimoto, J. Org. Chem., 2001, 66, 6775-6786.
9. C. Jiang, D. J. A. Schedler, P. E. Morris, A. H. A. Zayed and D. C. Baker, Carbohydr. Res., 1990, 207, 277-285;
10. J. C. Morris, P. S. Lei, H. X. Zhai, T. Y. Shen and K. Mensa-Wilmot, Biochem. Biophys. Res. Commun., 1998, 244, 873-876;
11. D. Lampe, C. S. Liu, M. F. Mahon and B. V. L. Potter, J. Chem. Soc., Perkin Trans. 1, 1996, 244, 1717-1727;
12. A. P. Kozikowski, A. H. Fauq, R. A. Wilcox and S. R. Nahorski, Bioorg. Med. Chem. Lett., 1995, 5, 1295-1300;
13. T. Eguchi, S. Sasaki, Z. Huang and K. Kakinuma, J. Org. Chem., 2002, 67, 3979-3984;
14. C. Kim, J. Haddad, S. B. Vakulenko, S. O. Meroueh, Y. Wu, H. Yan and S. Mobashery, Biochemistry, 2004, 43, 2373-2383;
15. H. W. Chen, Z. B. Zhao, T. M. Hallis, Z. H. Guo and H. W. Liu, Angew. Chem., Int. Ed., 2001, 40, 607-610.
16. D. A. Sawyer and B. V. L. Potter, J. Chem. Soc., Perkin Trans. 1, 1992, 40, 923-932.
17. A. P. Kozikowski, A. H. Fauq, G. Powis and D. C. Melder, J. Am. Chem. Soc., 1990, 112, 4528-4531;
18. C. L. Schengrund and P. Kovac, Carbohydr. Res., 1999, 319, 24-28.
19. K. Dax and M. Albert, Top. Curr. Chem., 2001, 215, 193-275.
20. M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188;
21. M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743;
22. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559.
23. S. Jiang, G. Singh, D. J. Boam and J. R. Coggins, Tetrahedron: Asymmetry, 1999, 10, 4087-4090;
24. L. Begum, J. M. Box, M. G. B. Drew, L. M. Harwood, J. L. Humphreys, D. J. Lowes, G. A. Morris, P. M. Redon, F. M. Walker and R. C. Whitehead, Tetrahedron, 2003, 59, 4827-4841;
25. R. H. Rich, B. M. Lawrence and P. A. Bartlett, J. Org. Chem., 1994, 59, 693-694;
26. J. L. Humphreys, D. J. Lowes, K. A. Wesson and R. C. Whitehead, Tetrahedron Lett., 2004, 45, 3429-3432.
27. Radical methods: A. Arnone, P. Bravo, F. Viani, M. Zanda, G. Cavicchio and M. Crucianelli, J. Fluorine Chem., 1996, 76, 169-173;
28. T. Morikawa, Y. Kodama, J. Uchida, M. Takano, Y. Washio and T. Taguchi, Tetrahedron, 1992, 48, 8915-8926;
29. F. Barth and C. O-Yang, Tetrahedron Lett., 1991, 32, 5873-5876;
30. aldol methods: D. Saleur, T. Brigaud, J. P. Bouillon and C. Portella, Synlett, 1999, 32, 432-434.
31. For RCM approaches to cyclic difluorocompounds, see: S. Fustero, A. Navarro, B. Pina, J. G. Soler, A. Bartolome, A. Asensio, A. Simon, P. Bravo, G. Fronza, A. Volonterio and M. Zanda, Org. Lett., 2001, 3, 2621-2624;
32. Y. Y. Yang, W. D. Meng and F. L. Qing, Org. Lett., 2004, 6, 4257-4259;
33. Z. W. You, Y. Y. Wu and F. L. Qing, Tetrahedron Lett., 2004, 45, 9479-9481;
34. B. M. Kariuki, W. M. Owton, J. M. Percy, S. Pintat, C. A. Smith, N. S. Spencer, A. C. Thomas and M. Watson, Chem. Commun., 2002, 45, 228-229;
35. C. Audouard, J. Fawcett, G. A. Griffith, E. Kerouredan, A. Miah, J. M. Percy and H. L. Yang, Org. Lett., 2004, 6, 4269-4272;
36. R. W. Wang and F.-L. Qing, Org. Lett., 2005, 7, 2189-2192;
37. G. A. Griffith, J. M. Percy, S. Pintat, C. A. Smith, N. Spencer and E. Uneyama, Org. Biomol. Chem., 2005, 3, 2701-2712.
38. G. Q. Shi and M. Schlosser, Tetrahedron, 1993, 49, 1445-1456.
39. F. Q. Jin, Y. Y. Xu and W. Y. Huang, J. Fluorine Chem., 1995, 71, 1-4;
40. W. Dmowski, V. A. Manko and I. Nowak, J. Fluorine Chem., 1998, 88, 143-151;
41. H. Amii, T. Kobayashi, H. Terasawa and K. Uneyama, Org. Lett., 2001, 3, 3103-3105;
42. T. Ernet, A. H. Maulitz, E. U. Wurthwein and G. Haufe, J. Chem. Soc., Perkin Trans. 1, 2001, 3, 1929-1938;
43. M. Essers and G. Haufe, J. Chem. Soc., Perkin Trans. 1, 2002, 3, 2719-2728;
44. M. Essers, C. Muck-Lichtenfeld and G. Haufe, J. Org. Chem., 2002, 67, 4715-4721;
45. T. Hanamoto, K. Korekoda, K. Nakata, K. Handa, Y. Koga and M. Kondo, J. Fluorine Chem., 2002, 118, 99-101;
46. P. J. Crowley, J. M. Percy and K. Stansfield, Tetrahedron Lett., 1996, 37, 8237-8240;
47. H. Ito, A. Saito and T. Taguchi, Tetrahedron: Asymmetry, 1998, 9, 1979-1987;
48. H. Ito, A. Saito and T. Taguchi, Tetrahedron: Asymmetry, 1998, 9, 1989-1994;
49. P. J. Crowley, J. M. Percy and K. Stansfield, Tetrahedron Lett., 1996, 37, 8233-8236;
50. M. Sridhar, K. L. Krishna and J. M. Rao, Tetrahedron, 2000, 56, 3539-3545.
51. J. Leroy, H. Molines and C. Wakselman, J. Org. Chem., 1987, 52, 290-292.
52. P. J. Crowley, A. C. Moralee, J. M. Percy and N. S. Spencer, Synlett, 2000, 52, 1737-1740.
53. A. Arany, P. J. Crowley, J. Fawcett, M. B. Hursthouse, B. M. Kariuki, M. E. Light, A. C. Moralee, J. M. Percy and V. Salafia, Org. Biomol. Chem., 2004, 2, 455-465.
54. O. Arjona and J. Plumet, Curr. Org. Chem., 2002, 6, 571-595 reviews the approach.
55. P. J. Crowley, J. Fawcett, B. M. Kariuki, A. C. Moralee, J. M. Percy and V. Salafia, Org. Lett., 2002, 4, 4125-4128 describes preliminary results.
56. P. B. Hopkins and P. L. Fuchs, J. Org. Chem., 1978, 43, 1208-1217.
57. M. Leclaire, P. Jean, R. Lopez, L. Ricard, H. Plessix and J. Y. Lallemand, Tetrahedron, 1995, 51, 6983-6998.
58. H. Suzuki, H. Satake, H. Uno and H. Shimizu, Bull. Chem. Soc. Jpn., 1987, 60, 4471-4473.
59. M. Bialecki and P. Vogel, Helv. Chim. Acta, 1995, 78, 325-343;
60. P. Vogel, A. F. Sevin, P. Kernen and M. Bialecki, Pure Appl. Chem., 1996, 68, 719-722.
61. A. Mele, G. Salani, F. Viani and P. Bravo, Magn. Reson. Chem., 1997, 35, 168-174;
62. H F;
63. H F coupling attributed to a through-space interaction.
64. A. S. Balnaves, M. J. Palmer and J. M. Percy, Chem. Commun., 1999, 83, 2183-2184.
65. A highly-optimised ternary solvent system (TMEDA-PhMe-DCM) was required for a related system: J. L. Acena, O. Arjona, R. F. Delapradilla, J. Plumet and A. Viso, J. Org. Chem., 1992, 57, 1945-1946.
66. N2′ ring openings of oxabicycloalkenes have been carried out successfully in the presence of remote alkoxide groups: O. Arjona, R. F. de la Pradilla, A. Martin-Domenech and J. Plumet, Tetrahedron, 1990, 46, 8187-8198;
67. M. Lautens and R. K. Belter, Tetrahedron Lett., 1992, 33, 2617-2620.
68. J. L. Acena, O. Arjona, R. F. Delapradilla, J. Plumet and A. Viso, J. Org. Chem., 1994, 59, 6419-6424;
69. J. L. Acena, O. Arjona, R. Manas and J. Plumet, J. Org. Chem., 2000, 65, 2580-2582.
70. C. M. G. Lofstrom, A. M. Ericsson, L. Bourrinet, S. K. Juntunen and J. E. Bäckvall, J. Org. Chem., 1995, 60, 3586-3591.
71. W. L. Jiang, D. A. Lantrip and P. L. Fuchs, Org. Lett., 2000, 2, 2181-2184.
72. Reductive desulfonations of vinyl or dienyl sulfones have been reported by a number of groups: J. L. Fabre and M. Julia, Tetrahedron Lett., 1983, 24, 4311-4314;
73. J. P. Marino, M. S. McClure, D. P. Holub, J. V. Comasseto and F. C. Tucci, J. Am. Chem. Soc., 2002, 124, 1664-1668;
74. R. Leung-Toung, Y. Z. Liu, J. M. Muchowski and Y. L. Wu, J. Org. Chem., 1998, 63, 3235-3250.
75. For a review, see: C. Najera and M. Yus, Tetrahedron, 1999, 55, 10547-10658. The more direct reductive desulfonation with ring opening was adopted instead because it is shorter and carries no risk of defluorination via one-electron reduction of the vinylsulfone.
76. M. E. Jung and L. J. Street, J. Am. Chem. Soc., 1984, 106, 8327-8329.
77. S. Mirsadeghi and B. Rickborn, J. Org. Chem., 1985, 50, 4340-4345.
78. M. E. Jung and V. C. Truc, Tetrahedron Lett., 1988, 29, 6059-6062.
79. G. H. Lee, H. K. Lee, E. B. Choi, B. T. Kim and C. S. Pak, Tetrahedron Lett., 1995, 36, 5607-5608.
80. To check against variation in reagent quality, the reactions were run side-by-side with reagents from the same batch with the same result.
81. MacSpartan Pro, Wavefunction Inc., Irvine, California, USA, 2000.
82. S. Woo and B. A. Keay, Synthesis, 1996, 36, 669-686.
83. D. A. Bors and A. Streitwieser, J. Am. Chem. Soc., 1986, 108, 1397-1404;
84. H. J. Gais, M. van Gumpel, M. Schleusner, G. Raabe, J. Runsink and C. Vermeeren, Eur. J. Org. Chem., 2001, 108, 4275-4303.
85. J. F. King, R. Rathore, Z. R. Guo, M. Q. Li and N. C. Payne, J. Am. Chem. Soc., 2000, 122, 10308-10324.
86. P. J. Kocienski, B. Lythgoe and I. Waterhouse, J. Chem. Soc., Perkin Trans. 1, 1980, 122, 1045-1050.
87. Williams and co-workers describe the reduction of an allylic sulfone which retains a hydroxyl group ß-to the C-S bond, though there may be a strong stereoelectronic influence on the outcome of the reaction, rather than simply allylic stabilisation: D. R. Williams and P. J. Coleman, Tetrahedron Lett., 1995, 36, 35-38;
88. D. R. Williams, D. L. Brown and J. W. Benbow, J. Am. Chem. Soc., 1989, 111, 1923-1925.
89. T. J. Tewson and M. J. Welch, J. Org. Chem., 1978, 43, 1090-1092.
90. V. VanRheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 43, 1973-1976.
91. J. K. Cha and N. S. Kim, Chem. Rev., 1995, 95, 1761-1795.
92. C. Audouard, J. Fawcett, G. A. Griffiths, J. M. Percy, S. Pintat and C. A. Smith, Org. Biomol. Chem., 2004, 2, 528-541.