Diastereoselective and enantiospecific synthesis of γ-substituted α,β-unsaturated nitriles from O-protected allylic cyanohydrins

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3837-3848

  Baeza, Alejandro ^a   Casas, Jesús ^a   Nájera, Carmen ^a   Sansano, José M ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

O-PROTECTED CYANOHYDRINS; REACTION CONDITIONS; UNSATURATED ALDEHYDES; UNSATURATED NITRILES;

CARBONATES; ISOMERS; PHOSPHATES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

2 HEXENAL; ACETIC ACID; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALLYL COMPOUND; BENZYLAMINE; CARBONIC ACID DERIVATIVE; CINNAMALDEHYDE; CROTONALDEHYDE; CYANOHYDRIN; DIBENZYLAMINE; IRIDIUM; MALONIC ACID DERIVATIVE; NITRILE; NITROGEN DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; PHOSPHATE; REAGENT; SODIUM AZIDE; SODIUM DERIVATIVE; SUCCINIMIDE DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; NITRILES;

EID: 33646524527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060239j     Document Type: Article

References (94)

1. Johnson, D. V.; Griengl, H. Tetrahedron 1997, 53, 617-624.
2. Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021-3024.
3. Fleming, F. F.; Wang, Q. Chem. Rev. 2003, 103, 2035-2077.
4. Tokuzaki, K.; Kanemitu, Y.; Yoshimitsu, T.; Nagaoka, H. Tetrahedron Lett. 2000, 41, 5923-5926.
5. Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 2003, 14, 2651-2657.
6. Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 2003, 14, 1095-1102.
7. (a) Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Angew. Chem., Int. Ed. 2004, 43, 1126-1129.
8. (b) Fleming, F. F.; Zhang, Z.; Wei, G.; Steward, O. W. Org. Lett. 2005, 7, 447-449.
9. Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924.
10. Deardorff, D. R.; Taniguchi, C. M.; Nelson, A. C.; Pace, A. P.; Kim, A. J.; Pace, A. K.; Jones, A.; Tafti, S. A.; Nguyen, C.; O'Connor, C.; Tang, J.; Chen, J. Tetrahedron: Asymmetry 2005, 16, 1655-1661.
11. (a) Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570-6571.
12. (b) Kotter, T.; Klein, A.; Giannis, A. Angew. Chem., Int. Ed. 1992, 31, 1391-1392.
13. Camps, P.; Muñoz-Tornero, D.; Sánchez, L. Tetrahedron: Asymmetry 2004, 15, 311-321 and references therein.
14. (a) Jasmin, L.; Wu, M. V.; Ohara, P. T. Curr. Drug Targets: CNS Neurol. Disord. 2004, 3, 487-505.
15. (b) Pharmaceuticals; McGuire, J. L., Ed.; Wiley-VCH: Weinheim, 2000.
16. Marcus, J.; van Meurs, P. J.; van den Nieuwendijk, A. M. C. H.; Porchet, M.; Brussee, J.; van der Gen, A. Tetrahedron 2000, 56, 2491-2495.
17. For racemic Wittig or Wittig-type reactions, see: (a) Grée, D.; Vallerie, L.; Grée, R.; Toupet, L.; Washington, I.; Pelicier, J.-P.; Villacampa, M.; Pérez, J. M.; Houk, K. N. J. Org. Chem. 2001, 66, 2374-2381.
18. (b) Cherkaoui, H.; Soufiaoui, M.; Grée, R. Tetrahedron 2001, 57, 2379-2383.
19. (a) Burgess, K.; Henderson, I. Tetrahedron: Asymmetry 1990, 1, 57-60.
20. (b) Burgess, K.; Cassidy, J.; Henderson, I. J. Org. Chem. 1991, 56, 2050-2058.
21. For other uses of α-(arylsufinyl)acetonitrile in the racemic synthesis, see: (a) Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890-7893.
22. (b) Nokami, J.; Mandai, T.; Nishimura, A.; Takeda, T.; Wakabayashi, S. J. Am. Chem. Soc. 1986, 27, 5109-5112.
23. (c) Trost, B. M.; Tometzki, G. B. Synthesis 1991, 1235-1245.
24. (d) Rodríguez-Rivero, M.; Carretero, J. C. J. Org. Chem. 2003, 68, 2975-2978.
25. (e) Adrio, J.; Rodríguez-Rivero, M.; Carretero, J. C. Org. Lett. 2005, 7, 431-434.
26. (a) Tiecco, M.; Testaferri, L.; Marini, F.; Sand, C.; Bagnoli, L.; Temperini, A.; Tomassini, C. Eur. J. Org. Chem. 1998, 2275-2277.
27. (b) Tiecco, M.; Testaferri, L.; Marini, F.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 1999, 10, 747-757.
28. For the racemic selective γ-oxyselenation-deselenylation examples, see: (a) Tiecco, M.; Testaferri, L.; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun. 1993, 637-638.
29. (b) Fleming, F. F.; Wang, Q.; Zhang, Z.; Steward, O. W. J. Org. Chem. 2002, 67, 5953-5956.
30. (c) Fleming, F. F.; Wang, Q.; Steward, O. W. J. Org. Chem. 2003, 68, 4235-4238.
31. For different selective oxidations, see: Matsushita, Y.; Sugamoto, K.; Nakama, T.; Sakamoto, T.; Matsui, T. Tetrahedron Lett. 1995, 36, 1879-1882.
32. Urabe, H.; Matsuda, T.; Sato, F. Tetrahedron Lett. 1992, 33, 4179-4182.
33. For other racemic processes involving cyanomethyloxiranes, see: (a) Larcheveque, M.; Perriot, P.; Petit, Y. Synthesis 1983, 297-299.
34. (b) Fleming, F. F.; Wang, Q.; Steward, O. W. J. Org. Chem. 2001, 66, 2171-2174.
35. (a) Tanikaga, R.; Hosoya, K.; Kaji, A. Chem. Lett. 1987, 829-832.
36. (b) Kang, S. K.; Lee, D. H.; Kim, Y. S. C. Synth. Commun. 1992, 22, 1109-1113.
37. (a) Yamakawa, I.; Urabe, H.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1991, 32, 2045-2048.
38. (b) Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-415.
39. Gais, H.-J.; Bondarev, O.; Hetzer, R. Tetrahedron Lett. 2005, 46, 6279-6283.
40. For other racemic procedures catalyzed by palladium complexes, see: (a) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573-2574.
41. (b) Keinan, E.; Roth, Z. J. Org. Chem. 1983, 48, 1769-1772.
42. (c) Keinan, E.; Sahai, M.; Roth, Z. J. Org. Chem. 1985, 50, 3558-3566.
43. (d) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523-1529.
44. (e) Deardorff, D. R.; Taniguchi, C. M.; Tafti, S. A.; Kim, H. Y.; Choi, S. Y.; Downey, K. J.; Nguyen, T. V. J. Org. Chem. 2001, 66, 7191-7194.
45. Abe, H.; Nitta, H.; Mori, A.; Inoue, S. Chem. Lett. 1992, 2443-2446.
46. (a) Casas, J.; Baeza, A.; Sansano, J. M.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197-200.
47. (b) Casas, J.; Baeza, A.; Nájera, C.; Sansano, J. M.; Saá, J. M. Eur. J. Org. Chem. 2006, 1949-1958.
48. (a) Baeza A.; Casas J.; Nájera, C.; Sansano, J. M.; Saá, J. M. Angew. Chem., Int. Ed. 2003, 42, 3143-3146.
49. (b) Baeza, A.; Nájera, C.; Sansano, J. M.; Saá, J. M. Chem.-Eur. J. 2005, 11, 3849-386.
50. (a) Handbook of Organopalladium Chemistry for Organic Systems; Negishi, E., Ed.; Wiley: New York, 2002; Vol. II, Chapter V.2, p 1669.
51. (b) Tsuji, J. Palladium Reagents and Catalysis; Wiley: Chichester, 2004.
52. (c) Paquin, J.-F.; Lautens, M. Comprehensive Asymmetric Catalysis, Supplement 2; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 2004; pp 73-95.
53. For recent reviews of asymmetric palladium-catalyzed allylic substitutions, see: (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
54. (b) Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837.
55. (c) Miyabe, H.; Takemoto, Y. Synlett 2005, 1641-1655.
56. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 1995; p 22.
57. For recent reviews of the synthesis and applications of cyanohydrins and their derivatives, see: (a) North, M. Synlett 1993, 807-820.
58. (b) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1563.
59. (c) Gregory, R. J. H. Chem. Rev. 1999, 99, 3649-3682.
60. (d) North, M. Tetrahedron: Asymmetry 2003, 14, 147-176.
61. (e) Poechlauer, P.; Skranc, W.; Wubbolts, M. Asymmetric Catalysis on Industrial Scale; Blaser H. U., Schmidt, E., Eds.; Wiley-VCH: Weinheim, 2004; pp 151-164.
62. (f) North, M. Science of Synthesis; Murahashi, S.-I., Ed.; Thieme: Stuttgart, 2004; Vol. 19, pp 235-284.
63. (g) Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed. 2004, 43, 2752-2778.
64. (h) Synthesis and Applications of Non-Racemic Cyanohydrins and α-Ammo Acids. Tetrahedron Symposium in Print; North, M., Ed.; 2004, 60, 10371-10568.
65. For reviews about bifunctional catalysis, see: (a) Gröger, H. Chem.-Eur. J. 2001, 7, 5246-5251.
66. (b) Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
67. (c) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1189-1199.
68. (d) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 3-15.
69. (e) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491-1508.
70. (a) Micó, I.; Nájera, C. Tetrahedron 1993, 49, 4327-4322.
71. (b) Baeza, A.; Nájera, C.; Sansano, J. M. ARKIVOC 2005, ix, 353-363.
72. Abiko, Y.; Yamahiwa, N.; Sugita, M.; Tian, J.; Matsunaga, S.; Shibasaki, M. Synlett 2004, 2434-2436.
73. For some examples of synthetic applications of the racemic cyanohydrin-O-phosphates, see: (Preparation of other nitrites) (a) Harusawa, S.; Yoneda, R.; Kurihara, T.; Hamada, Y.; Shiori, T. Tetrahedron Lett. 1984, 25, 427-428.
74. (b) Yoneda, R.; Harusawa, S.; Kurihara, T. J. Chem. Soc., Perkin Trans. 1 1988, 3163-3168.
75. (c) Yoneda, R.; Osaki, H.; Harusawa, S.; Kurihara, T. J. Chem. Soc., Perkin Trans. 1 1990, 607-610.
76. (d) Yoneda, R.; Harusawa, S.; Kurihara, T. J. Org. Chem. 1991, 56, 1827-1832.
77. (In Friedel-Crafts acylations and [3,3]-sigmatropic rearrangements): (e) Kurihara, T.; Harusawa, S.; Hirai, J.; Yoneda, R. J. Chem. Soc., Perkin Trans. 1 1987, 1771-1776.
78. (f) Kurihara, T.; Miki, M.; Santo, K.; Harusawa, S.; Yoneda, R. Chem. Pharm. Bull. 1986, 34, 4620-4628.
79. (g) Kurihara, T.; Miki, M.; Yoneda, R.; Harusawa, S. Chem. Pharm. Bull. 1986, 34, 2747-2753.
80. (h) Kurihara, T.; Santo, K.; Harusawa, S.; Yoneda, R. Chem. Pharm. Bull. 1987, 35, 4777-4788.
81. (i) Yoneda, R.; Santo, K.; Harusawa, S.; Kurihara, T. Synth. Commun. 1987, 17, 921-92.
82. (In heterocyclic synthesis): (j) Kurihara, T.; Hanakawa, M.; Harusawa, S.; Yoneda, R. Chem. Pharm. Bull. 1983, 31, 2932-2935.
83. The reactivity as α-acyl anion synthon of a cyanohydrin-O-chiral- cyclic-amidophosphate has been reported: (a) Schrader, T. Angew. Chem., Int. Ed. 1995, 34, 917-919.
84. (b) Schrader, T. Chem.-Eur. J. 1997, 3, 1273-1282.
85. (a) Miyabe, H.; Matsumura, A.; Moriyama, K.; Takemoto, Y. Org. Lett. 2004, 6, 4631-4634.
86. (b) Lipowski, G.; Helmchem, G. Chem. Commun. 2004, 116-117.
87. (c) Miyabe, H.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. J. Org. Chem. 2005, 70, 2148-2153.
88. Leahy, D. K.; Evans, P. A. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 191-214.
89. Kondo, T.; Mitsudo, T. Ruthenium in Organic Synthesis; Wiley VCH: Weinheim, 2004; pp 129-151.
90. (a) Belda, P. A.; Moberg, C. Acc. Chem. Res. 2004, 37, 159-167.
91. (b) Krska, S. W.; Hughes, D.; Reamer, R. A.; Mathre, D. J.; Palucki, M.; Yasuda, N.; Sun, Y.; Trost, B. M. Pure Appl. Chem. 2004, 76, 625-633.
92. Cantat, T.; Agenet, N.; Jutand, A.; Pleixats, R.; Moreno-Mañas, M. Eur. J. Org. Chem. 2005, 4277-4286.
93. The racemization of cyanohydrin-O-phosphate derived from benzaldehyde has been evaluated in the presence of 1 equiv of nitrogenated bases at room temperature, in THF (under an inert atmosphere) during 12 h. The results of the table below clearly demonstrate a stronger basic character of the benzylamine and triethylamine versus dibenzylamine, N-methylimidazole (NMI), and pyridine. (Equation Presented)
94. Handbook of Organopalladium Chemistry for Organic Systems; Negishi, E., Ed.; Wiley: New York, 2002; Vol. II, Chapter VII.3, p 2783.