(1R,3R)-2-Methylene-1,3-dithiolane 1,3-dioxide: A highly reactive and highly selective chiral ketene equivalent in cycloaddition reactions with a broad range of dienes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1998, Pages 2771-2781

  Aggarwal, Varinder K ^a   Gültekin, Zeynep ^a   Grainger, Richard S ^a   Adams, Harry ^a   Spargo, Peter L ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748648417     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804607g     Document Type: Article

References (66)

1. For a review see: S. Ranganathan, D. Ranganathan and A. K. Mehrotra, Synthesis, 1977, 289.
2. (a) E. Viera and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865;
3. (b) J. L. Reymond and P. Vogel, J. Chem. Soc., Chem. Commun., 1990, 1070;
4. (c) P. Vogel, D. Fattori, F. Gasparini and C. Le Drain, Synlett, 1990, 173;
5. (d) J. L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729.
6. (a) J. Mattay, J. Mertes and G. Maas, Chem. Ber., 1989, 122, 327;
7. (b) W. R. Roush, A. P. Essenfeld, J. S. Warmus and B. B. Brown, Tetrahedron Lett., 1989, 20, 7305.
8. (a) C. Maignan and R. A. Raphael, Tetrahedron, 1983, 39, 3245;
9. (b) R. V. Williams and X. Lin, J. Chem. Soc., Chem. Commun., 1989, 1872;
10. (c) N. Katagiri, S. Ise, N. Watanabe and C. Kaneko, Chem. Pharm. Bull., 1990, 38, 3242;
11. (d) O. De Lucci, D. Fabbri and V. Lucchini, Synlett, 1991, 565.
12. For a review see O. De Lucchi and L. Pasquato, Tetrahedron, 1988, 44, 6755.
13. (a) C. Maignan and F. Belkasmioui, Tetrahedron Lett., 1988, 29, 2823;
14. (b) A. W. M. Lee, W. H. Chan and M. S. Wong, J. Chem. Soc., Chem. Commun., 1988, 1585.
15. (a) H. B. Kagan and B. Ronan, Tetrahedron: Asymmetry, 1991, 2, 75;
16. (b) H. B. Kagan and B. Ronan, Tetrahedron: Asymmetry, 1992, 3, 115.
17. R. Lopez and J. C. Carretero, Tetrahedron: Asymmetry, 1991, 2, 93.
18. Y. Arai, S. Kuwayama, Y. Takeuchi and T. Koizumi, Synth. Commun., 1986, 16, 233.
19. J. Martynow, M. Dimitroff and A. G. Fallis, Tetrahedron Lett., 1993, 34, 8201.
20. V. K. Aggarwal, M. Lightowler and S. D. Lindell, Synlett, 1992, 730.
21. For a preliminary account see: V. K. Aggarwal, J. Drabowicz, R. S. Grainger, Z. Gültekin, M. Lightowler and P. L. Spargo, J. Org. Chem., 1995, 60, 4962.
22. The experimental details for this synthesis are described in: V. K. Aggarwal, R. S. Grainger, H. Adams and P. L. Spargo, J. Org. Chem., 1998, 63, 3481.
23. K. R. Dahnke and L. A. Paquette, Org. Synth., 1992, 71, 175.
24. V. K. Aggarwal, I. W. Davies, R. Franklin, J. Maddock, M. F. Mahon and K. C. Molloy, J. Chem. Soc., Perkin Trans. 1, 1994, 2363.
25. V. K. Aggarwal, S. Schade and H. Adams, J. Org. Chem., 1997, 62, 1139.
26. (a) F. Di Furia, G. Modena and R. Seraglia, Synthesis, 1984, 325;
27. (b) F. Di Furia, G. Licini and G. Modena, Gazz. Chim. Ital., 1990, 120, 165;
28. (c) M. Corich, F. Di Furia, G. Licini and G. Modena, Tetrahedron Lett., 1992, 33, 3043.
29. V. K. Aggarwal, G. Evans, E. Moya and J. Dowden, J. Org. Chem., 1992, 57, 6390.
30. V. Conte, F. Di Furia, G. Licini, G. Modena, G. Sbampato and G. Valle, Tetrahedron: Asymmetry, 1991, 2, 257.
31. (a) N. Komatsu, M. Hashizume, T. Sugita and S. Uemura, J. Org. Chem., 1993, 58, 4529;
32. (b) A. Scettri, F. Bonadies, A. Lattanzi, A. Senatore and A. Soriente, Tetrahedron: Asymmetry, 1996, 7, 657;
33. (c) A. Lattanzi, F. Bonadies, A. Senatore, A. Soriente and A. Scettri, Tetrahedron: Asymmetry, 1997, 8, 2473.
34. (a) S. Kobayashi, Y. Fujishita and T. Mukaiyama, Chem. Lett., 1990, 1455;
35. (b) S. Kobayashi, M. Furuya, A. Ohtsuba and T. Mukaiyama, Tetrahedron: Asymmetry, 1992, 2, 115.
36. Full crystallographic details, excluding structure factor tables, have been deposited at the Cambridge Crystallographic Data Centre (CCDC). For details of the deposition scheme, see 'Instructions for Authors', J. Chem. Soc., Perkin Trans. 1, available via the RSC Web pages (http//www.rsc.org/authors). Any request to the CCDC for this material should quote the full literature citation and the reference number 207/241.
37. For other examples of selective Diels-Alder reactions resulting from the difference in size between a sulfinyl oxygen and a lone pair see: (a) A. Waldner, Tetrahedron Lett., 1989, 30, 3061;
38. (b) ref. 9;
39. (c) M. J. Fisher, W. J. Hehre, S. D. Kahn and L. E. Overman, J. Am. Chem, Soc., 1988, 110, 4625;
40. For an example where addition occurs syn to a sulfinyl oxygen see: A. M. Naperstkow, J. B. Macaulay, M. J. Newlands and A. G. Fallis, Tetrahedron Lett., 1989, 30, 5077.
41. M. A. McCarrick, Y. D. Wu and K. N. Houk, J. Am. Chem. Soc., 1992, 114, 1499.
42. R. J. Sundberg and J. D. Bloom, J. Org. Chem., 1981, 46, 4836.
43. For reviews on Diels-Alder reactions of dihydropyridines see: D. M. Stout and A. I. Meyers, Chem. Rev., 1982, 82, 223;
44. see also B. Weinstein, L. C. Lin and F. W. Fowler, J. Org. Chem., 1980, 45, 1657;
45. E. W. Baxter, D. Labaree, S. Chao and P. S. Mariano, J. Org. Chem., 1989, 54, 2893;
46. G. R. Krow, J. T. Carey, K. C. Cannon and K. J. Henz, Tetrahedron Lett., 1982, 23, 2527.
47. See summary in: F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, Toronto, 1990.
48. D. A. Evans, W. L. Scott and L. K. Truesdale, Tetrahedron Lett., 1972, 13, 121.
49. For a review see: K. Afarinkia, V. Vinader, T. D. Nelson and G. H. Posner, Tetrahedron, 1992, 48, 9111.
50. For a review on sulfoxide reduction see: M. Madesclaire, Tetrahedron, 1988, 44, 6537.
51. (a) D. O. Spry, J. Chem. Soc., Chem. Commun., 1973, 671;
52. (b) D. O. Spry, Tetrahedron Lett., 1973, 14, 2413.
53. F. Mohanazadeh, A. R. Momeni and Y. Ranjbar, Tetrahedron Lett., 1994, 35, 6127.
54. G. V. Kaiser, R. D. G. Cooper, R. E. Koehler, C. F. Murphy, J. A. Webber, I. G. Wright and E. M. Van Heyningen, J. Org. Chem., 1970, 35, 2430.
55. J. Drabowicz and S. Oae, Synthesis, 1977, 404.
56. A. Nayak, B. Nanda, N. B. Das and R. P. Sharma, J. Chem. Res. (S), 1994, 100.
57. (a) E. De Guchteneere, D. Fattori and P. Vogel, Tetrahedron, 1992, 48, 10 603;
58. (b) F. Emery and P. Vogel, J. Org. Chem., 1995, 60, 5843;
59. (c) V. Moritz and P. Vogel, Tetrahedron Lett., 1992, 33, 5243;
60. (c) P. Renaud and J. P. Vionnet, J. Org. Chem., 1993, 58, 5895;
61. (d) P. Vogel and J. L. Reymond, J. Chem. Soc., Chem. Commun., 1990, 1070;
62. (e) Y. Chen and P. Vogel, Tetrahedron Lett., 1992, 33, 4917.
63. G. M. Sheldrick, University of Gottingen, Germany, 1993. SHELXL93, an integrated system for solving and refining crystal structures from diffraction data.
64. E. J. Corey and T.-P. Loh, J. Am. Chem. Soc., 1991, 113, 8966;
65. see also: C. Le Drian and A. E. Greene, J. Am. Chem. Soc., 1982, 104, 5473.
66. E. Vicira and P. Vogel, Helv. Chim. Acta, 1982, 65, 1701.