Cycloaddition reactions of a nitrogen-substituted oxyallyl cation with cyclopentadiene and substituted furans. Reaction conditions, diastereoselectivity, regioselectivity, and transition state modeling

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1478-1482

  Walters, Michael A ^a   Arcand, Helene R ^a  

^a Dartmouth College ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000059785     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951609z     Document Type: Article

References (56)

1. Several reviews have appeared which describe this methodology: (a) Hosomi, A.; Tominga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Mann, J. Tetrahedron 1986, 42, 4611-4659. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-88. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66.
2. Several reviews have appeared which describe this methodology: (a) Hosomi, A.; Tominga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Mann, J. Tetrahedron 1986, 42, 4611-4659. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-88. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66.
3. Several reviews have appeared which describe this methodology: (a) Hosomi, A.; Tominga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Mann, J. Tetrahedron 1986, 42, 4611-4659. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-88. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66.
4. Several reviews have appeared which describe this methodology: (a) Hosomi, A.; Tominga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Mann, J. Tetrahedron 1986, 42, 4611-4659. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-88. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66.
5. Several reviews have appeared which describe this methodology: (a) Hosomi, A.; Tominga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Mann, J. Tetrahedron 1986, 42, 4611-4659. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-88. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66.
6. Some examples include: (a) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. (b) Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411-4412. (c) Sato, T.; Hayakawa, Y.; Noyori, E. Bull. Chem. Soc. Jpn. 1984, 57, 2515-2525. (d) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228. (e) Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
7. Some examples include: (a) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. (b) Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411-4412. (c) Sato, T.; Hayakawa, Y.; Noyori, E. Bull. Chem. Soc. Jpn. 1984, 57, 2515-2525. (d) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228. (e) Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
8. Some examples include: (a) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. (b) Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411-4412. (c) Sato, T.; Hayakawa, Y.; Noyori, E. Bull. Chem. Soc. Jpn. 1984, 57, 2515-2525. (d) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228. (e) Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
9. Some examples include: (a) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. (b) Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411-4412. (c) Sato, T.; Hayakawa, Y.; Noyori, E. Bull. Chem. Soc. Jpn. 1984, 57, 2515-2525. (d) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228. (e) Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
10. Some examples include: (a) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 36, 4185-4188. (b) Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411-4412. (c) Sato, T.; Hayakawa, Y.; Noyori, E. Bull. Chem. Soc. Jpn. 1984, 57, 2515-2525. (d) White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226-228. (e) Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075-2083.
11. Walters, M. A.; Arcand, H. R.; Lawrie, D. J. Tetrahedron Lett. 1995, 36, 23-26.
12. Sasaki, T.; Ishibashi, Y.; Ohno, M. Tetrahedron Lett. 1982, 23, 1693-1696.
13. Murray, D. H.; Albizati, K. Tetrahedron Lett. 1990, 31, 4109-4112.
14. Föhlisch, B.; Krimmer, D.; Gehrlach, E.; Kashammer, D. Chem. Ber. 1988, 121, 1585-1593.
15. Harmata, M.; Fletcher, V.; Claassen, R. J. J. Am. Chem. Soc. 1991, 113, 9861-9862.
16. Hardinger, S. A.; Bayne, C.; Kantorowski, E.; MeClellan, R.; Larres, L.; Nuesse, M.-A. J. Org. Chem. 1995, 60, 1104-1105.
17. For example, nitrogen substituants play an important role in the reactivity of the enamine C=C with electrophiles: (a) Adam, W.; Ahrweiler, M.; Paulini, K.; Reissig, H.-U.; Voerckel, V. Chem. Ber. 1992, 125, 2719-2721. (b) Lenz, G. R. Synthesis 1978, 489-518.
18. For example, nitrogen substituants play an important role in the reactivity of the enamine C=C with electrophiles: (a) Adam, W.; Ahrweiler, M.; Paulini, K.; Reissig, H.-U.; Voerckel, V. Chem. Ber. 1992, 125, 2719-2721. (b) Lenz, G. R. Synthesis 1978, 489-518.
19. For example, attachment of a chiral oxazolidinone auxiliary might be possible. See: Palomo, C.; Berree, F.; Linden, A.; Villalgordo, J. M. J. Chem. Soc., Chem. Commun. 1994, 1861-1862 and references cited therein.
20. Sheehan, J. C.; Bolhofer, W. A. J. Am. Chem. Soc. 1950, 72, 2786-2788.
21. Gaudry, M.; Marquet, A. Tetrahedron 1970, 26, 5611-5615.
22. Gabriel, S. Chem. Ber. 1911, 1905-1915.
23. Bowers, K. G.; Mann, J.; Markson, A. J. J. Chem. Res., Synop. 1986, 424-425.
24. Föhlisch, B.; Gottstein, W.; Herter, R.; Wanner, I. J. Chem. Res., Synop. 1981, 246.
25. 2 as an effective catalyst for some organic transformations.
26. 2 as an effective catalyst for some organic transformations.
27. 2 as an effective catalyst for some organic transformations.
28. 2 as an effective catalyst for some organic transformations.
29. 2 as an effective catalyst for some organic transformations.
30. 2 as an effective catalyst for some organic transformations.
31. Desimoni, G.; Faita, G.; Righetti, P. P.; Tacconi, G. Tetrahedron 1991, 47, 8399-8406.
32. + as a Lewis acid in the Diels-Alder cycloaddition reaction, see: Forman, M. A.; Dailey, W. P. J. Am. Chem. Soc. 1991, 113, 2761-2762.
33. + as a Lewis acid in the Diels-Alder cycloaddition reaction, see: Forman, M. A.; Dailey, W. P. J. Am. Chem. Soc. 1991, 113, 2761-2762.
34. 1b,c
35. 13C resonances associated with the C=O of the phthalimide group were not easily observable in several of the cycloadducts in which this moiety occupied the equatorial position. (The exception to this observation is compound 15b.) All other analytical data obtained on these equatorial diastereomers were consistent with their assigned structure.
36. Takaya, H.; Makino, S.; Hayakawa, Y.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1766-1777.
37. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976. For a lucid explanation of the application of FMO theory to regioselectivity in the Diels-Alder reaction see: Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092-4094. The reaction of iron-stabilized oxyallyl cations with monosubstituted cyclic dienes has been investigated. It was found that FMO theory (CNDO/2) could be employed to rationalize the regioselectivity observed in all but one of the reported examples. Noyori, R., Shimizu, F.; Fukuta, K.; Takaya, H.; Hayakawa, Y. J. Am. Chem. Soc. 1977, 99, 5196-5198.
38. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976. For a lucid explanation of the application of FMO theory to regioselectivity in the Diels-Alder reaction see: Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092-4094. The reaction of iron-stabilized oxyallyl cations with monosubstituted cyclic dienes has been investigated. It was found that FMO theory (CNDO/2) could be employed to rationalize the regioselectivity observed in all but one of the reported examples. Noyori, R., Shimizu, F.; Fukuta, K.; Takaya, H.; Hayakawa, Y. J. Am. Chem. Soc. 1977, 99, 5196-5198.
39. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976. For a lucid explanation of the application of FMO theory to regioselectivity in the Diels-Alder reaction see: Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092-4094. The reaction of iron-stabilized oxyallyl cations with monosubstituted cyclic dienes has been investigated. It was found that FMO theory (CNDO/2) could be employed to rationalize the regioselectivity observed in all but one of the reported examples. Noyori, R., Shimizu, F.; Fukuta, K.; Takaya, H.; Hayakawa, Y. J. Am. Chem. Soc. 1977, 99, 5196-5198.
40. This is the first published example of the reaction of an oxyallyl cation with this oxygenated diene. This process, however, is not particular to the nitrogen-substituted species 1. For example, Lautens has observed the cycloaddition of 2-methoxyfuran with a dialkyl-substituted oxyallyl cation. (Lautens, M. Personal communication, University of Toronto.
41. 3N) were very low, but the products obtained were consistent with the model described.
42. PM3; (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-64. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-20. PM3 was recently parameterized for lithium (c) Anders, E.; Kock, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301-1312. This new Li/PM3 parameter set has been employed by Anders to study monolithiated sulfones, sulfoxides, and 1,3-dithanes: Koch, R.; Anders, E. J. Org. Chem. 1994, 59, 4529-4534.
43. PM3; (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-64. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-20. PM3 was recently parameterized for lithium (c) Anders, E.; Kock, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301-1312. This new Li/PM3 parameter set has been employed by Anders to study monolithiated sulfones, sulfoxides, and 1,3-dithanes: Koch, R.; Anders, E. J. Org. Chem. 1994, 59, 4529-4534.
44. PM3; (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-64. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-20. PM3 was recently parameterized for lithium (c) Anders, E.; Kock, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301-1312. This new Li/PM3 parameter set has been employed by Anders to study monolithiated sulfones, sulfoxides, and 1,3-dithanes: Koch, R.; Anders, E. J. Org. Chem. 1994, 59, 4529-4534.
45. PM3; (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-64. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-20. PM3 was recently parameterized for lithium (c) Anders, E.; Kock, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301-1312. This new Li/PM3 parameter set has been employed by Anders to study monolithiated sulfones, sulfoxides, and 1,3-dithanes: Koch, R.; Anders, E. J. Org. Chem. 1994, 59, 4529-4534.
46. The PM3 method has recently been applied to the reaction of pyridine N-oxides with dipolarophiles: (a) Matsuoka, T.; Harano, K.; Hisano, T. Heterocycles 1994, 37, 257-264. (b) Matsuoka, T.; Harano, K. Tetrahedron 1995, 51, 6451-6458.
47. The PM3 method has recently been applied to the reaction of pyridine N-oxides with dipolarophiles: (a) Matsuoka, T.; Harano, K.; Hisano, T. Heterocycles 1994, 37, 257-264. (b) Matsuoka, T.; Harano, K. Tetrahedron 1995, 51, 6451-6458.
48. SPARTAN 3.1: Hehre, W. J.; Burke, L. D.; Shusterman, A. J. Wavefunction, Inc., Irvine, CA.
49. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
50. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
51. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
52. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
53. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
54. Oxyallyl cations and related reactive intermediates have been studied at the ab initio level of theory by several groups. (a) Goodman, J. M.; Hoffmann, H. M. R.; Vinter, J. G. Tetrahedron Lett. 1995, 36, 7757-7760. (b) Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgenson, W. L. J Am. Chem. Soc. 1994, 116, 3494-3499. (c) Coolidge, M. B.; Yamashita, K.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1990, 112, 1751-1754. (d) Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1991, 113, 5950-5958. (e) Ichimura, A. S.; Lahti, P. M.; Matlin, A. R. J. Am. Chem. Soc. 1990, 112, 2868-2875. (f) Janoschek, R., Kalcher, J. Int. J. Quantum Chem. 1990, 38, 653-664.
55. This is the same effect on frontier molecular orbital energy as observed in computational studies relating to the Lewis acid catalyzed Diels-Alder reaction. Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094-4096.
56. + was associated only with the oxyallyl cation oxygen. Full details of these calculations will be published shortly.