Intramolecular 4 + 3 cycloadditions. Cycloaddition reactions of cyclic alkoxyallylic and oxyallylic cations

Journal of the American Chemical Society

Volumn 118, Issue 12, 1996, Pages 2860-2871

  Harmata, Michael ^a   Elomari, Saleh ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001604648     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952740r     Document Type: Article

References (73)

1. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
2. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
3. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
4. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
5. For reviews of 4 + 3 cycloadditions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
6. For a review of intramolecular 4 + 3 cycloadditions, see: Harmata, M. In Advances in Cycloaddition: Lautens, M., Ed.; JAI: Greenwich, CT, 1996; Vol. 4 (in press).
7. For reviews of intramolecular Diels-Alder reactions, see: (a) Roush, W. R. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 4.4.
8. For reviews of intramolecular Diels-Alder reactions, see: (a) Roush, W. R. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, Chapter 4.4.
9. (a) Harmata, M.; Gamlath, C. B.; Barnes, C. L.; Jones, D. E. J. Org. Chem 1995, 60, 5077.
10. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
11. (c) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241.
12. (d) Harmara, M.; Herron B. F. J. Org. Chem. 1993, 58, 7393.
13. (e) Harmata, M.; Herron, B. F. Tetrahedron Lett. 1993, 34, 5381.
14. (f) Harmata, M.; Herron, B. F. Synthesis 1993, 202.
15. (g) Harmata, M.; Elahmad, S. Tetrahedron Lett. 1993, 34, 789.
16. (h) Harmata, M.; Gamlath, C. B.; Barnes, C. L. Tetrahedron Lett. 1993, 34, 265.
17. (i) Harmata, M.; Fletcher, V. R.; Claassen, R J., II J. Am. Chem. Soc. 1991, 113, 9861.
18. (j) Harmata, M.; Gamlath, C. B.; Barnes, C. L. Tetrahedron Lett. 1990, 31, 5981.
19. (k) Harmata, M.; Gamlath, C. B. J. Org. Chem. 1988, 53, 6154.
20. Crandall, J. K.; Haseltine, R. P. J. Am. Chem Soc. 1968, 90, 6251.
21. (a) Barber, L. L.; Chapman, O. L.; Lassila, J D. J. Am Chem. Soc. 1969, 91, 3664.
22. (b) Chapman, O. L.; Clardy, J. C.; McDowell, T. L.; Wright, H. E. J. Am. Chem. Soc. 1973, 95, 5086.
23. (c) Barltrop, J. A.; Day, A. C.; Samuel, C. J. J. Am. Chem. Soc. 1979, 101, 7521.
24. (a) Schultz, A. G.; Reilly, J. J. Am. Chem. Soc. 1992, 114, 5068.
25. (b) Schultz, A. G.; Macielag, M.; Plummer, M. J. Org. Chem. 1988, 53, 391.
26. (c) West, F. G.; Hartker-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem, 1993, 58, 6795.
27. (a) Noyori, R.; Taba, Y.; Makino, S.; Takaya, H. Tetrahedron Lett. 1973, 14, 1741.
28. (b) Ito, S.; Ohtani. H.; Amiya, S. Tetrahedron Lett. 1973, 14, 1737.
29. (c) Vinter, J. G.; Hoffmann, H. M. R. J. Am. Chem. Soc. 1974, 96, 5466.
30. (a) Fohlisch, B., Joachim, R. Chem. Ber. 1987, 96, 5466.
31. (b) Föhlisch, B.; Gottsein, W.; Kaiser, R.; Wanner, T. Tetrahedron Lett 1980, 21, 1951.
32. (c) Föhlisch, B.; Joachimi, R.; Reiner, S. J. Chem. Soc. (S) 1993, 253.
33. (d) Matzinger, P.; Eugster, C. M. Helv. Chim. Acta 1979, 62, 2325.
34. Levisalles J.; Rose, E.; Tkatchenko, I. Chem. Commun. 1969, 445.
35. (a) Schmid, R.; Schmid, H. Helv. Chim. Acta 1974, 57, 1883.
36. (b) Ernst, B.; Ganter, C. Helv. Chem. Acta 1978, 61, 1775.
37. (a) Jin, S.-j.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
38. (b) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
39. (c) Oh, J.; Cha, J. K. Synlett 1994, 967.
40. (d) Lee, J.; Oh, J.; Jin, S.-j.; Choi, J.-R.; Atwood, J. L.; Cha, J. K. J. Org. Chem. 1994, 59, 6955.
41. (e) Oh, J.; Lee, J.; Jin, S.-j.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3449.
42. (f) Oh, J.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1992, 57, 6664.
43. 4 and found that it does not give the same product as that from the reaction of 7. Studies of the reactions of the cycloadducts with Lewis acids continue and will be reported elsewhere.
44. (a) Kaiser, R.; Föhlisch, B. Helv. Chim. Acta 1990, 73, 1504.
45. (b) Föhlisch, B.; Hetter, R. Chem. Ber. 1984, 117, 2580.
46. (c) Föhlisch, B.; Flogaus, R.; Oexle, J.; Schadel, A. Tetrahedron Lett. 1984, 25, 1773.
47. (d) Föhlisch, B.; Gehrlach, E.; Herter, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 137.
48. Krapcho, A P.; Weimaster, J. F.; Eldridge, J. M.; Jahngen, E. G. E., Jr., Lovey, A. J.; Stephens, W. P. J. Org. Chem. 1978, 48, 138.
49. Wender P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771.
50. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, U.K., 1983; p 190.
51. (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1.
52. (b) Warnhoff, E. W.; Martin, D G.; Johnson, W. S. In Organic Syntheses Collective Volume 4; Rabjohn, N., Ed., Wiley: New York, 1963; pp 162-66.
53. -1; F(000) = 440; temperature = 23/-1°; final R = 0.050 for 1056 reflections with 1 > 2σ(I).
54. As a cautionary note, it must be pointed out that we have not rigorously established that the cycloaddition reactions involving cyclopentenyl cations are under kinetic control or that the mechanism of the reaction is indeed concerted.
55. Other factors could certainly be involved. Further studies are needed to paint a complete picture of the basis of simple diastereoselection in these reactions.
56. -1; F(000) = 471.95; radiation = Cu Kα (λ = 1.540 56) Å; temperature = 23/-1°; final R = 0.041 for 2095 reflections with 1 > 2.5σ(I).
57. -3; radiation = Cu Ka (λ = 1.540 56) Å; temperature = 23/-1°; final R = 0.049 for 2831 reflections with 1 > 2.0σ(I).
58. Base (yield. 23a:23b); pyridine (12%, 1:9.3); diisopropylethylamine (11%, 1:9.8); 2,6-lutidine (9%, 1:9.8); 2,6-di-tert-butylpyridine (11%, 1:9.6).
59. Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
60. Harmata, M.; Elomari, S.; Barnes, C. L. Acta Crystallogr., C (submitted).
61. 8c The first letter denotes the conformation of the tetrahydropyranone portion of the molecule, boat (B) or chair (C). The subscripts describe the orientation of the polymethylene chain joining the positions α to the carbonyl group of the tetrahydropyranone, axial (a) and/or equatorial (e).
62. Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757.
63. -3; radiation = Mo Kα (0.709 30) Å; temperature = 23/-1°; final R = 0.043 for 1886 reflections with 1 > 2.0σ(I).
64. Harmata, M.; Barnes, C. L.; Elomari, S. J. Chem. Crystallogr. (manuscript in preparation).
65. Funk, R. L.; Bolton, G. L.; Brummond, K. M.; Ellstead, K. E.; Stallman, J. B. J. Am. Chem. Soc. 1993, 115, 7024.
66. Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381
67. Koch, S. S. C.; Chamberlin, R. Synth. Commun. 1989, 289.
68. For the experimental details of the preparation of the dienyl iodide used to make 44. see the supporting information.
69. -1: radiation = Mo Kα (0.709 30) Å; temperature = 23/-1°; final R = 0.047 for 2537 reflections with I > 2.0σ(I).
70. For the experimental details of the preparation of the dienyl iodide used to make 48, see the supporting information.
71. -1; radiation = Mo Kα (λ = 0.709 30) Å; temperature = 23/-1°; final R = 0.059 for 1686 reflections with 1 > 2σ(I).
72. Burpitt, R. D.; Thweatt, J. G. In Organic Syntheses Collective Volume 5; Baumgarten, H. E., Ed.; Wiley: New York, 1973; pp 277-80.
73. Still, W C.; Kahn, M., Mitra, A. J. Org. Chem. 1978, 43, 2923.