Synthesis of secondary E-allylamines and β-aminophosphorylated compounds from β-functionalized enamines derived from phosphonium salts, phosphine oxides and phosphonates

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9609-9628

  Palacios, Francisco ^a   Aparicio, Domitila ^a   García, Jesús ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLAMINE; ENAMINE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHONIUM DERIVATIVE;

ARTICLE; PHOSPHORYLATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030575347     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00498-X     Document Type: Article

References (68)

1. 1. a) For an excellent review see: Cheikh, R. B.; Chaabauni, R.; Laurent, A.; Misin, P.; Nafti, A. Synthesis, 1983, 685.
2. b) Bergdahl, M.; Hett, R.; Friebe, T. L.; Gangloff, A. R.; Iqbal, J.; Wu, Y.; Helquist, P. Tetrahedron Lett., 1993, 34, 7371.
3. 2. a) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc., 1992, 114, 6568.
4. b) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett., 1996, 33, 703.
5. 3. For an excellent review, see: Stütz, A., Angew. Chem. Int. Ed. Engl., 1987, 26, 320.
6. 4. a) Bargar, T. A.; Broersma, R. J.; Creemer, L. C.; McCarthy, J. R.; Hornsperger, J. M.; Palfreyman, M. G.; Wagner, J.; Yung, M. G. J. Med. Chem., 1986, 29, 315.
7. b) Ohba, T.; Ikeda, F.; Wakoyama, J.; Takei, H. Bioorg. Med. Chem. Lett., 1996, 6, 219.
8. 5. a) Stütz, A.; Petranyi, G. J. Med. Chem., 1984, 27, 1539.
9. b) Petranyi, G.; Ryder, N. S., Stütz, A. Science, 1984, 224, 1239.
10. c) Stütz, A.; Georgopoulos, A.; Granitzer, W.; Petranyi, G.; Berney, D. J. Med. Chem., 1986, 29, 112.
11. 6. Lemaire-Audoire, S.; Savignac, M.; Genêt, J. P.; Bernard, J. M. Tetrahedron Lett., 1995, 36, 8765.
12. 7. a) Reetz M. T.; Röhring, D.; Harms, K.; Frenking, G. Tetrahedron Lett., 1994, 35, 1267.
13. b) Burgers, K.; Lui, L. T.; Pal, B. J. Org. Chem., 1993, 58, 4758.
14. c) Reetz M. T.; Röhring, D. Angew. Chem. Int. Ed. Engl., 1989, 28, 1706.
15. d) Koskinen, A. M. P.; Pihko, P. M. Tetrahedron Lett., 1994, 35, 7417.
16. e) Lemaire-Audoire, S.; Savignac, M.; Genêt, J. P. Synlett, 1996, 75.
17. 8. a) Wei, Z. Y.; Knaus, E. E. Tetrahedron Lett., 1993, 34, 4439.
18. b) Huwe, C. M.; Blechert, S. Tetrahedron Lett., 1994, 35, 9537. Huwe, C. M.; Kichl, D. C.; Blechert, S. Synlett, 1996, 65.
19. b) Huwe, C. M.; Blechert, S. Tetrahedron Lett., 1994, 35, 9537. Huwe, C. M.; Kichl, D. C.; Blechert, S. Synlett, 1996, 65.
20. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
21. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
22. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
23. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
24. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
25. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
26. 9. For recent contributions see: Mukhopadhyay, M.; Reddy, H. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem., 1995, 60, 2670. Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725. Ründig, E. P.; Xu, L. H.; Schnell, B. Synlett, 1994, 413. Takai, K; Odaka, H.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett., 1994, 35, 1893. Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem., 1994, 59, 4007. Jumnah, R.; Willians, J. M. J.; Willians, A. C. Tetrahedron Lett., 1993, 34, 6619. Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem., 1989, 54, 3292.
27. 10. For recent contributions see: Bell, K. E.; Knight, D. W.; Gravestock, H. B. Tetrahedron Lett., 1995, 36, 8681. Katrizky, A. R.; Chang, H. X.; Verin, S. V. Tetrahedron Lett., 1995, 36, 343. Van Beuthem, R. A. T. H.; Michels, J. J.; Hiermstra, H; Speckamp, W. N. Synlett, 1994, 368. Alcón, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A., Tetrahedron Lett., 1994, 35, 1589. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc., 1991, 113, 3526.
28. 10. For recent contributions see: Bell, K. E.; Knight, D. W.; Gravestock, H. B. Tetrahedron Lett., 1995, 36, 8681. Katrizky, A. R.; Chang, H. X.; Verin, S. V. Tetrahedron Lett., 1995, 36, 343. Van Beuthem, R. A. T. H.; Michels, J. J.; Hiermstra, H; Speckamp, W. N. Synlett, 1994, 368. Alcón, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A., Tetrahedron Lett., 1994, 35, 1589. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc., 1991, 113, 3526.
29. 10. For recent contributions see: Bell, K. E.; Knight, D. W.; Gravestock, H. B. Tetrahedron Lett., 1995, 36, 8681. Katrizky, A. R.; Chang, H. X.; Verin, S. V. Tetrahedron Lett., 1995, 36, 343. Van Beuthem, R. A. T. H.; Michels, J. J.; Hiermstra, H; Speckamp, W. N. Synlett, 1994, 368. Alcón, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A., Tetrahedron Lett., 1994, 35, 1589. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc., 1991, 113, 3526.
30. 10. For recent contributions see: Bell, K. E.; Knight, D. W.; Gravestock, H. B. Tetrahedron Lett., 1995, 36, 8681. Katrizky, A. R.; Chang, H. X.; Verin, S. V. Tetrahedron Lett., 1995, 36, 343. Van Beuthem, R. A. T. H.; Michels, J. J.; Hiermstra, H; Speckamp, W. N. Synlett, 1994, 368. Alcón, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A., Tetrahedron Lett., 1994, 35, 1589. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc., 1991, 113, 3526.
31. 10. For recent contributions see: Bell, K. E.; Knight, D. W.; Gravestock, H. B. Tetrahedron Lett., 1995, 36, 8681. Katrizky, A. R.; Chang, H. X.; Verin, S. V. Tetrahedron Lett., 1995, 36, 343. Van Beuthem, R. A. T. H.; Michels, J. J.; Hiermstra, H; Speckamp, W. N. Synlett, 1994, 368. Alcón, M.; Canas, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A., Tetrahedron Lett., 1994, 35, 1589. Whitesell, J. K.; Yaser, H. K. J. Am. Chem. Soc., 1991, 113, 3526.
32. 11. a) Wei, Z. Y.; Knaus, E. E.; Synlett, 1994, 345.
33. b) Wei, Z. Y.; Knaus, E. E.; Tetrahedron Lett., 1994, 35, 2305.
34. 12. a) Linderman, R. J.; Meyers, A. I. Tetrahedron Lett., 1983, 24, 3043.
35. b) Cavalla, D.; Cruse, V. B.; Warren, S. J. Chem. Soc. Perkin Trans I, 1987, 1893.
36. 13. For recent contributions see: a) Palacios, F.; Pérez de Heredia, I.; Rubiales, G. J. Org. Chem., 1995, 60, 2384.
37. b) Palacios, F.; Alonso, C.; Rubiales, G. Tetrahedron, 1995, 51, 3683.
38. c) Palacios, F.; Aparicio, D.; de los Santos, J.M., Tetrahedron, 1996, 52, 4857.
39. 14. a) Palacios, F.; Aparicio, D.; de los Santos, J.M., Tetrahedron, 1996, 52, 4123.
40. b) Palacios, F.; Garcia, J.; Ochoa de Retana, A.; Oyarzabal, J. Heterocycles, 1995, 41, 1915.
41. c) Barluenga, J.; Lopez, F.; Palacios, F., Chem. Commun., 1985, 1681.
42. d) Barluenga, J.; Lopez, F.; Palacios, F., Tetrahedron Lett., 1987, 28, 2875.
43. 15. a) Palacios, F.; Aparicio, D.; de los Santos, J.M., Tetrahedron Lett., 1996, 37, 1289.
44. b) Palacios, F.; Aparicio, D.; de los Santos, J.M., Tetrahedron, 1994, 50, 12727.
45. c) Lopez, F.; Pelaez, E.; Palacios, F.; Barluenga, J.; García, S.; Tejerina, B.; García, A., J. Org. Chem., 1994, 59, 1984.
46. d) Barluenga, J.; Merino, I.; Palacios, F., Tetrahedron Lett., 1990, 31, 6713.
47. e) Barluenga, J.; Merino, I.; Palacios, F., Tetrahedron Lett., 1989, 30, 5493.
48. 16. Preliminary results: Palacios, F.; Aparicio, D.; García, J., Synlett., 1994, 260.
49. 16 have been reported, a very specific example of preparation of primary Ε-allylamines appeared, which involved the homologation of β-imino phosphonates into azadienes followed by reduction with sodium borohydride; Shin, W. S.; Lee, K.; Oh, D. Y. Tetrahedron Lett., 1995, 36, 281.
50. 18. Barluenga, J.; Merino, I.; Palacios, F. J. Chem. Soc. Perkin Trans I, 1991, 341. Duncan, M.; Gallagher, M. J. Org. Mag. Res., 1981, 15, 37.
51. 18. Barluenga, J.; Merino, I.; Palacios, F. J. Chem. Soc. Perkin Trans I, 1991, 341. Duncan, M.; Gallagher, M. J. Org. Mag. Res., 1981, 15, 37.
52. 19. For an excellent monograph on this topic see: Johnson, A. W.; Kaska, W. C.; Ostoga Starzewski, K. A.; Dixon, D. A. in "Ylides and Imines of Phosphorus". Wiley, New York, 1993.
53. 20. For a recent review see: Pitacco, G.; Valentin, E. in "The Chemistry of Enamines". Ed. Z. Rappoport, Willey, Chichester, 1994, p. 923.
54. 21. a) Yamauchi, K.; Ohtsuki, S.; Kinoshita, H. J. Org. Chem., 1984, 49, 1158.
55. b) Patel, D. V.; Rielly-Gawyin, K.; Ryono, D. E. Tetrahedron Lett., 1990, 31, 5587.
56. c) Patel, D. V.; Rielly-Gawyin, K.; Ryono, D. E. Bioorg. Med. Chem. Lett., 1993, 3, 2051.
57. d) Monaghan, D. T.; Bridges, R. J.; Cotman, C. W. Ann. Rev. Pharmacol. Toxicol., 1989, 29, 365.
58. e) Neidlein, R.; Li, S. Helv. Chim. Acta, 1994, 77, 1570 and references therein cited.
59. 22. Neidlein, R.; Greulich, P.; Arch. Pharm. (Weinhein), 1994, 327, 709. van der Klem, P. A. M.; Dreef, C. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett., 1989, 30, 5473. Xu, Y.; Jiang, X.; Yuan, C. Synthesis, 1990, 427.
60. 22. Neidlein, R.; Greulich, P.; Arch. Pharm. (Weinhein), 1994, 327, 709. van der Klem, P. A. M.; Dreef, C. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett., 1989, 30, 5473. Xu, Y.; Jiang, X.; Yuan, C. Synthesis, 1990, 427.
61. 22. Neidlein, R.; Greulich, P.; Arch. Pharm. (Weinhein), 1994, 327, 709. van der Klem, P. A. M.; Dreef, C. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett., 1989, 30, 5473. Xu, Y.; Jiang, X.; Yuan, C. Synthesis, 1990, 427.
62. 23. Hua, D. H.; Bharathi, S. V.; Robinson, P. D.; Tsujimoto, A.; J. Org. Chem., 1990, 55, 2128.
63. 24. Fuller, J. C.; Belisle, C. H.; Goralski, C. T.; Singaran, B.; Tetrahedron Lett., 1994, 35, 5389. Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Berkhardt, F. R.; Goralski, C. T.; Singaran, B. J. Org. Chem., 1994, 59, 6378.
64. 24. Fuller, J. C.; Belisle, C. H.; Goralski, C. T.; Singaran, B.; Tetrahedron Lett., 1994, 35, 5389. Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Berkhardt, F. R.; Goralski, C. T.; Singaran, B. J. Org. Chem., 1994, 59, 6378.
65. 25. Clayden, J.; McElroy, A. B.; Warren, S. J. Chem. Perkin Trans I, 1995, 1913. Amstrong, S. K.; Collington, E. W.; Knight, J. G.; Naylor, A.; Warren, S. J. Chem. Perkin Trans I, 1993, 1433.
66. 25. Clayden, J.; McElroy, A. B.; Warren, S. J. Chem. Perkin Trans I, 1995, 1913. Amstrong, S. K.; Collington, E. W.; Knight, J. G.; Naylor, A.; Warren, S. J. Chem. Perkin Trans I, 1993, 1433.
67. 26. Mitchell, H.; Warren, S. Tetrahedron Lett., 1996, 37, 2105.
68. 27. For an excellent review see: Martin, S. F. in "Comprehensive Organic Synthesis". Trost, B. M.; Fleming, I.; Heathcock, C. H. Eds. Pergamon Press, Oxford, Vol. 2, 1991, p. 475.