The first sequential reaction promoted by manganese: Complete stereoselective synthesis of (E)-α,β-unsaturated esters from 2,2-dichloroesters and aldehydes

Journal of Organic Chemistry

Volumn 72, Issue 12, 2007, Pages 4396-4400

  Concellón, José M ^a   Rodríguez Solla, Humberto ^a   Díaz, Pamela ^a   Llavona, Ricardo ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROESTERS; DOUBLE BONDS; STEREOSELECTIVE SYNTHESIS;

ALDEHYDES; MANGANESE; STEREOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ESTERS;

2,2 DICHLOROESTER DERIVATIVE; ALDEHYDE; ESTER DERIVATIVE; MANGANESE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34250211446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070209w     Document Type: Article

References (77)

1. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049-7052.
2. To see some synthetic applications of manganese: (a) Kakiya, H.; Nishimae, S.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 8807-8815.
3. (b) Kim, S.-H.; Rieke, R. D. J. Org. Chem. 2000, 65, 2322-2330.
4. (c) Guijarro, A.; Gómez, C.; Yus, M. Trends Org. Chem. 2000, 8, 65-91.
5. (d) Cahiez, G.; Martín, A.; Delacroix, T. Tetrahedron Lett. 1999, 40, 6407-6410.
6. (e) Kim, S.-H.; Rieke, R. D. Synth. Commun. 1998, 28, 1065-1072.
7. (f) Kim, S.-H.; Rieke, R. D. J. Org. Chem. 1998, 63, 6766-6767.
8. (g) Tang, J.; Shinokubo, H.; Oshima, K. Synlett 1998, 1075-1076.
9. (h) Rieke, R. D.; Kim, S.-H. J. Org. Chem. 1998, 63, 5235-5239.
10. (i) Kim, S.-H.; Rieke, R. D. Tetrahedron Lett. 1997, 38, 993-996.
11. (j) Suh, Y.; Rieke, R. D. Tetrahedron Lett. 2004, 45, 1807-1809.
12. For preparations of active manganese (Mn*), see: (a) Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012.
13. (b) Kim, S. -H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200.
14. (c) Tang, J.; Shinokubo, H.; Oshima, K. Tetrahedron 1999, 55, 1893-1904 and reference 2d therein.
15. The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1968; Vol. 2.
16. (a) Aggarwal, V. K.; Fulton, J. R.; Sheldon, C. G.; de Vicente, J. J. Am. Chem. Soc. 2003, 125, 6034-6035.
17. (b) Hon, Y.-S.; Lu, L.; Chang, R.-C.; Lin, S.-W.; Sun, P.-P.; Lee, C.-F. Tetrahedron 2000, 56, 9269-9279.
18. (c) Soucy, F.; Grenier, L.; Behnke, M. L.; Destree, A. T.; McCormack, T. A.; Adams, J.; Plamondon, L. J. Am. Chem. Soc. 1999, 121, 9967-9976.
19. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann./Recl. 1997, 1283-1301.
20. (e) Spinella, A.; Fortunati, T.; Soriente, A. Synlett 1997, 93-94.
21. (f) Patil, V. J.; Mävers, U. Tetrahedron Lett. 1996, 37, 1281-1284.
22. (a) Ferguson, M. L.; Senecal, T. D.; Groendyke, T. M.; Mapp, A. K. J. Am. Chem. Soc. 2006, 128, 4576-4577.
23. (b) List, B.; Doehring, A.; Fonseca, M. T. H.; Job, A.; Torres, R. R. Tetrahedron 2006, 62, 476-482.
24. (c) Ando, K. J. Org. Chem. 1999, 64, 6815-6821.
25. (d) Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
26. (e) Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108.
27. (a) Karimi, B.; Enders, D. Org. Lett. 2006, 8, 1237-1240.
28. (b) Li, J.-H.; Wang, D.-P.; Xie, Y.-X. Tetrahedron Lett. 2005, 46, 4941-4944.
29. (c) Moreno-Mañas, M.; Pérez, M.; Pleixants, R. Tetrahedron Lett. 1996, 37, 7449-7452.
30. (d) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 635-638.
31. (a) Guevel, A. C.; Hart, D. J. J. Org. Chem. 1996, 61, 465-472.
32. (b) Welch, J. T.; Herbert, R. W. J. Org. Chem. 1990, 55, 4782-4784.
33. (c) Chenera, B.; Chuang, C.; Hart, D. J.; Lai, C. J. Org. Chem. 1992, 57, 2018-2029.
34. (d) Palomo, C.; Aizpurúa, J. M.; García, J. M.; Gamboa, I.; Cossio, F. P.; Lecea, B.; López, C. J. Org. Chem. 1990, 55, 2498-2503.
35. (a) Tamooka, K.; Nagasawa, A.; Wei, S.; Nakai, T. Tetrahedron Lett. 1996, 37, 8895-8898.
36. (b) Tamooka, K.; Nagasawa, A.; Wei, S.; Nakai, T. Tetrahedron Lett. 1996, 37, 8899-8900.
37. (a) Zeitler, K. Org. Lett. 2006, 8, 637-640.
38. (b) Katrizky, A. R.; Feng, D.; Lang, H. J. Org. Chem. 1997, 62, 715-720.
39. (c) Perisamy, M.; Radhakrishnan, U.; Rameshkumar, C.; Brunet, J. Tetrahedron Lett. 1997, 38, 1623-1626.
40. (a) Trost, B. M.; Parquette, J. R. J. Org. Chem. 1993, 58, 1579-1681.
41. (b) Tanikaga, R.; Miyashita, K.; Ono, N.; Kaji, A. Synthesis 1982, 131-132.
42. (c) Tanaka K.; Uneme, H.; Ono, N.; Kaji, A. Chem. Lett. 1979, 1039-1040.
43. (a) Feuillet, F. J. P.; Cheeseman, M.; Mahon, M. F.; Bull, S. D. Org. Biomol. Chem. 2005, 3, 2976-2989.
44. (b) Feuillet, F. J. P.; Robinson, D. E. J. E.; Bull, S. D. Chem. Commun. 2003, 2184-2185.
45. (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
46. (b) Straus, D. A.; Grubbs, R. H. J. Mol. Catal. 1985, 28, 9-19.
47. (c) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733-1744.
48. Concellón, J. M.; Rodríguez-Solla, H.; del Amo, V. Synlett 2006, 315-317.
49. The reaction between an enolate derived from a 2-bromoester and the carbonyl compound affords, in high yields, the corresponding 2,3-epoxyester (Darzens' reaction) as the major product instead of the desirable 2-bromo-3-hydroxyester, consequently the reaction must be carried out at low temperatures (-90 °C).
50. (a) Concellón, J. M.; Concellón, C.; Méjica, C. J. Org. Chem. 2005, 70, 6111-6113.
51. (b) Barma, D. K.; Kundu, A.; Bandyopadhyay, A.; Kundu, A.; Sangras, B.; Briot, A.; Mioskowski, C.; Falck, J. R. Tetrahedron Lett. 2004, 45, 5917-5920.
52. (c) Only one example (ethyl 3-phenylprop-2-enoate) has been synthesised using a sequential reaction of ethyl dibromoacetate and benzaldehyde promoted by Fe(0): Falk, J. R.; Bejot, D. K.; Bandyopadhyay, A.; Joseph, S.; Mioskowski, C. J. Org. Chem. 2006, 71, 8178-8182.
53. (d) Using a zinc-metal-promoted olefination: Ishino, Y.; Mihara, M.; Nishihama, S.; Nishiguchi, I. Bull. Chem. Soc. Jpn. 1998, 71, 2669-2672.
54. 2-promoted sequential reactions, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 92, 307-338.
55. (b) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354;
56. 2 see: (c) Krief, A.; Laval, A. M. Chem. Rev. 1999, 99, 745-777.
57. (d) Steel, P. G.; J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751.
58. (e) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372.
59. (f) Concellón, J. M.; Rodríguez-Solla, H. Chem. Soc. Rev. 2004, 33, 599-609.
60. (g) Dahlén, A.; Hilmerson, G. Eur. J. Inorg. Chem. 2004, 3393-3403.
61. 2, see: (a) Takai, K. Org. React. 2004, 64, 253-612.
62. (b) Liu, Y.; Wu, H.; Zhang, Y. Synth. Commun. 2001, 31, 47-52.
63. (c) Matsubara, S.; Oshima, K. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 5.
64. (d) Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
65. (e) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1-36.
66. 2-promoted sequential reactions: (f) Barma, D. K.; Kundu, A.; Bandyopadhyay, A.; Sangras, B.; Briot, A.; Mioskowski, C.; Falck, J. R. Tetrahedron Lett. 2004, 45, 5917-5920.
67. (g) Barma, D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. J. Am. Chem. Soc. 2003, 125, 3218-3219.
68. To see a recent Fe(0)-mediated sequential reaction (utilized in the synthesis of ethyl 3-phenylprop-2-enoate), see ref 16c.
69. 2-CHCOCl.
70. Compounds 2a and 2b were available from commercial sources.
71. The coupling constant between the olefmic protons of compounds 3 were in accordance with the average literature values: Silverstein, R. M.; Bassler, G. C.; Morrill T. C. In Spectrometric Identification of Organic Compounds; John Wiley and Sons: New York, 1991; Chapter 4, Appendix F, p 221. In addition, values of coupling constants of olefmic protons were in accordance with the values described in the literature for analogous alkenes, see references 5b, 5c, 10a, 16, and 25.
72. 2 (prepared by the method described in Concellón, J. M.; Rodríguez-Solla, H.; Bardales, E.; Huerta, M. Eur. J. Org. Chem. 2003, 1775-1778), 1.1 euro; 1 mmol Mn* (prepared by the method described in reference 2d), 0.5 euro.
73. Wittig reactions carried out with enolizable carbonyl compounds can generate alkenes in very low yield: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
74. Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775.
75. Parham, W. E.; Twelves, R. R. J. Org. Chem. 1957, 22, 730-734.
76. Tezuka, Y.; Hashimoto, A.; Ushizaka, K.; Imai, K. J. Org. Chem. 1990, 55, 329-333.
77. Castelani, P.; Comasseto, J. V. Tetrahedron 2005, 61, 2319-2326.