'Nonbiomimetic' oxidations of dihydropyridines

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10001-10005

  Lavilla, Rodolfo ^a   Báron, Xavier ^a   Coll, Oscar ^a   Gullón, Francisco ^a   Masdeu, Carme ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032567316     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980688m     Document Type: Article

References (61)

1. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
2. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
3. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
4. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
5. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
6. For reviews on the chemistry of dihydropyridines, see: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. (c) Sausins, A.; Duburs, G. Khim. Geterotsikl. Soedin. 1993, 579. (d) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291. (e) Kutney, J. P. Heterocycles 1977, 7, 593. (f) Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199.
7. For a preliminary report of a part of this work, see: Lavilla, R.; Gullón, F.; Barón, X.; Bosch, J. Chem. Commun. 1997, 213.
8. (a) Lavilla, R.; Coll, O.; Kumar, R.; Bosch, J. J. Org. Chem. 1998, 63, 2728.
9. (b) Lavilla, R.; Kumar, R.; Coll, O.; Masdeu, C.; Bosch, J., Molins, E.; Espinosa, E. Unpublished results.
10. 4 were not successfully reproduced in our hands: (a) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 684 (Chem. Abstr. 1969, 70, 11513) (b) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr. 1969, 70, 28776).
11. 4 were not successfully reproduced in our hands: (a) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 684 (Chem. Abstr. 1969, 70, 11513) (b) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr. 1969, 70, 28776).
12. 4 were not successfully reproduced in our hands: (a) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 684 (Chem. Abstr. 1969, 70, 11513) (b) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr. 1969, 70, 28776).
13. 4 were not successfully reproduced in our hands: (a) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 684 (Chem. Abstr. 1969, 70, 11513) (b) Negievich, L. A.; Grishin, O. M.; Yasnikov, A. A. Ukr. Khim. Zh. 1968, 34, 802 (Chem. Abstr. 1969, 70, 28776).
14. For a 4 + 2 cycloaddition involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: (a) Natsume, M.; Sekine, Y.; Ogawa, M.; Soyagimi, H.; Kitagawa, Y. Tetrahedron Lett. 1979, 3473. (b) Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992, 33, 349. For the osmylation of N-acyl-1,2-dihydropyridines, see: (c) Tschamber, T.; Backenstrass, F.; Neuburger, M.; Zehnder, M.; Streith, J. Tetrahedron 1994, 50, 1135. (d) Tschamber, T.; Rodríguez-Pérez, E.-M.; Wolf, P.; Streith. J. Heterocycles 1996, 42, 669.
15. For a 4 + 2 cycloaddition involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: (a) Natsume, M.; Sekine, Y.; Ogawa, M.; Soyagimi, H.; Kitagawa, Y. Tetrahedron Lett. 1979, 3473. (b) Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992, 33, 349. For the osmylation of N-acyl-1,2-dihydropyridines, see: (c) Tschamber, T.; Backenstrass, F.; Neuburger, M.; Zehnder, M.; Streith, J. Tetrahedron 1994, 50, 1135. (d) Tschamber, T.; Rodríguez-Pérez, E.-M.; Wolf, P.; Streith. J. Heterocycles 1996, 42, 669.
16. For a 4 + 2 cycloaddition involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: (a) Natsume, M.; Sekine, Y.; Ogawa, M.; Soyagimi, H.; Kitagawa, Y. Tetrahedron Lett. 1979, 3473. (b) Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992, 33, 349. For the osmylation of N-acyl-1,2-dihydropyridines, see: (c) Tschamber, T.; Backenstrass, F.; Neuburger, M.; Zehnder, M.; Streith, J. Tetrahedron 1994, 50, 1135. (d) Tschamber, T.; Rodríguez-Pérez, E.-M.; Wolf, P.; Streith. J. Heterocycles 1996, 42, 669.
17. For a 4 + 2 cycloaddition involving N-acyl-1,2-dihydropyridines and singlet oxygen, see: (a) Natsume, M.; Sekine, Y.; Ogawa, M.; Soyagimi, H.; Kitagawa, Y. Tetrahedron Lett. 1979, 3473. (b) Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992, 33, 349. For the osmylation of N-acyl-1,2-dihydropyridines, see: (c) Tschamber, T.; Backenstrass, F.; Neuburger, M.; Zehnder, M.; Streith, J. Tetrahedron 1994, 50, 1135. (d) Tschamber, T.; Rodríguez-Pérez, E.-M.; Wolf, P.; Streith. J. Heterocycles 1996, 42, 669.
18. Fowler, F. W. J. Org. Chem. 1972, 37, 1321.
19. The o-nitrophenylsulfonyl group was selected because of its easy and mild cleavage; see: Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
20. Knaus, E. E.; Redda, K. Can. J. Chem. 1977, 55, 1788.
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23. For a general review on the oxidation of enamines, see: Pittaco, G.; Valentin, E. V. In The Chemistry of Enamines; Rappoport, Z., Ed. (The Chemistry of Functional Groups, Patai, S.; Rappoport, Z., Eds.); Wiley: Chichester, 1994; Part 2, Chapter 17.
24. For a general review on the oxidation of enamines, see: Pittaco, G.; Valentin, E. V. In The Chemistry of Enamines; Rappoport, Z., Ed. (The Chemistry of Functional Groups, Patai, S.; Rappoport, Z., Eds.); Wiley: Chichester, 1994; Part 2, Chapter 17.
25. For a similar reaction taking place upon an N-acyl-1,2,3,4-tetrahydropyridine, see: Masamune, T.; Hayashi, H.; Takasugi, M.; Fukuoka, S. J. Org. Chem. 1972, 37, 2343.
26. The related interaction of peracids with enol ethers has been reported: (a) Wood, H. B., Jr.; Fletcher, H. G., Jr. J. Am. Chem. Soc. 1957, 79, 3234. (b) Groneberg, R. D.; Miyazaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwabuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593.
27. The related interaction of peracids with enol ethers has been reported: (a) Wood, H. B., Jr.; Fletcher, H. G., Jr. J. Am. Chem. Soc. 1957, 79, 3234. (b) Groneberg, R. D.; Miyazaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwabuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593.
28. Akashi, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2063.
29. For a discussion about the influence of conformational solvent effects and hydrogen-bonding in the stereocontrol of double dihydroxylations, see: (a) Donohoe, T. J.; Moore, P. R.; Beddoes, R. L. J. Chem. Soc., Perkin Trans. 1, 1997, 43. (b) Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.
30. For a discussion about the influence of conformational solvent effects and hydrogen-bonding in the stereocontrol of double dihydroxylations, see: (a) Donohoe, T. J.; Moore, P. R.; Beddoes, R. L. J. Chem. Soc., Perkin Trans. 1, 1997, 43. (b) Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.
31. +, 10), 245 (16), 204 (8), 91 (100).
32. See, for instance: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
33. Different versions of this transformation were investigated, following the protocols developed by Sharpless: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (c) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813. (d) Brucko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
34. Different versions of this transformation were investigated, following the protocols developed by Sharpless: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (c) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813. (d) Brucko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
35. Different versions of this transformation were investigated, following the protocols developed by Sharpless: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (c) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813. (d) Brucko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
36. Different versions of this transformation were investigated, following the protocols developed by Sharpless: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (c) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813. (d) Brucko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
37. (a) Crandall, J. K. In Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Ed. Wiley: Chichester, 1995, Vol. 3, p 2061.
38. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
39. (c) Murray, R. W. Chem. Rev. 1989, 89, 1187.
40. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
41. (a) Adam, W.; Peters, E.-M.; Peters, K.; von Schnering, H.-G.; Voerckel, V. Chem. Ber. 1992, 125, 1263.
42. (b) Adam, W.; Ahrweiler, M.; Paulini, K.; Reissig, H.-U.; Voerckel, V. Chem. Ber. 1992, 125, 2719.
43. (c) Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257.
44. (d) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255.
45. Adam, W.; Heil, M.; Hutterer, R. J. Org. Chem. 1992, 57, 4491.
46. DMD solutions were prepared according to Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377, and the dioxirane content (ca. 0.07 M) was determined by iodometric titration.
47. For the use of catalytic DMD epoxidations, see: (a) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (b) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
48. For the use of catalytic DMD epoxidations, see: (a) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (b) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
49. For the use of catalytic DMD epoxidations, see: (a) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (b) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
50. For the use of catalytic DMD epoxidations, see: (a) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887. (b) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
51. For related structures, see: (a) Koppenhoefer, B.; Winter, B.; Bayer, E. Liebigs Ann. Chem. 1983, 1986. (b) Adam, W.; Peters, K.; Sauter, M. Synthesis 1994, 111. (c) Agami, C.; Couty, F.; Hamon, L.; Prince, B.; Puchot, C. Tetrahedron 1990, 46, 7003. Also see refs 12 and 21c.
52. For related structures, see: (a) Koppenhoefer, B.; Winter, B.; Bayer, E. Liebigs Ann. Chem. 1983, 1986. (b) Adam, W.; Peters, K.; Sauter, M. Synthesis 1994, 111. (c) Agami, C.; Couty, F.; Hamon, L.; Prince, B.; Puchot, C. Tetrahedron 1990, 46, 7003. Also see refs 12 and 21c.
53. For related structures, see: (a) Koppenhoefer, B.; Winter, B.; Bayer, E. Liebigs Ann. Chem. 1983, 1986. (b) Adam, W.; Peters, K.; Sauter, M. Synthesis 1994, 111. (c) Agami, C.; Couty, F.; Hamon, L.; Prince, B.; Puchot, C. Tetrahedron 1990, 46, 7003. Also see refs 12 and 21c.
54. This transformation represents a two-step sequence for the anti-Markownikoff water addition to 1,4-dihydropyridines.
55. The preferred formation of trans isomers in this type of reactions may reflect the more favorable approach of the nucleophile from the less sterically hindered face of the iminium ion, away from the electron-rich hydroxyl group. See, for instance: Khan, S. D.; Dobbs, K. D.; Hehre, W. J. J. Am. Chem. Soc. 1988, 110, 4602. Also see ref 25c.
56. For related transformations, see: (a) Kozikowski, A. P.; Park, P. J. Org. Chem. 1984, 49, 1674. (b) Sakagami, H.; Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1433. (c) Hartman, G. D.; Philips, B. T.; Halczenko, W.; Springer, J. P.; Hirshfield, J. J. Org. Chem. 1987, 52, 1136.
57. For related transformations, see: (a) Kozikowski, A. P.; Park, P. J. Org. Chem. 1984, 49, 1674. (b) Sakagami, H.; Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1433. (c) Hartman, G. D.; Philips, B. T.; Halczenko, W.; Springer, J. P.; Hirshfield, J. J. Org. Chem. 1987, 52, 1136.
58. For related transformations, see: (a) Kozikowski, A. P.; Park, P. J. Org. Chem. 1984, 49, 1674. (b) Sakagami, H.; Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1433. (c) Hartman, G. D.; Philips, B. T.; Halczenko, W.; Springer, J. P.; Hirshfield, J. J. Org. Chem. 1987, 52, 1136.
59. Interestingly, when attempting the reaction at 0°C the only isolated compound (10%, NIvIR and MS evidence) was a bicyclic analogue of 15, bearing a (trimethylsilyl)methyl group at C-2, thus indicating that an intramolecular trapping of the carbocation by the hydroxyl group had taken place instead of the usual elimination to regenerate the double bond. For a related situation, see ref 28c.
60. For additions or addition-cyclization sequences of enol ethers to iminium ions, see: (a) Natsume, M.; Masashi, O. Heterocycles 1980, 14, 169. (b) Shono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S. J. Am. Chem. Soc. 1982, 104, 5753.
61. For additions or addition-cyclization sequences of enol ethers to iminium ions, see: (a) Natsume, M.; Masashi, O. Heterocycles 1980, 14, 169. (b) Shono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S. J. Am. Chem. Soc. 1982, 104, 5753.