Catalysed asymmetric protonation of simple linear keto-enolic species a route to chiral α-arylpropionic acids

European Journal of Organic Chemistry

Volumn , Issue 23, 2002, Pages 3986-3994

  Roy, Olivier ^a   Riahi, Abdelkhalek ^a   Hénin, Françoise ^a   Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Alkaloids; Asymmetric catalysis; Cleavage reactions; Decarboxylation; Protonation

Indexed keywords

ALKALOID; CINCHONINE; KETONE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; DECARBOXYLATION; ENANTIOSELECTIVITY; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0036898724     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200212)2002:23<3986::AID-EJOC3986>3.0.CO;2-L     Document Type: Article

References (66)

1. [1a] L. Duhamel, P. Duhamel, J.-C. Launay, J.-C. Plaquevent, Bull. Soc. Chim. Fr. 1984, II, 421-430.
2. [1b] C. Fehr, Chimia 1991, 45, 253-261.
3. [1c] S. Hünig, Methoden Org. Chem. (Houben-Weyl) 1996, vol. VII, p. 3887-3911.
4. [1d] C. Fehr, Angew Chem. Int. Ed. Engl. 1996, 35, 2566-2587.
5. [1e] A. Yanagisawa, K. Ishihara, H. Yamamoto, Synlett 1997, 411-420.
6. [1f] J. Eames, N. Weerasooriya, Tetrahedron: Asymmetry 2000, 12, 1-24.
7. Alkyllithium cleavage of silyl enol ethers or enol acetates and chiral protic sources: [2a] A. Yanagisawa, T. Watanabe, T. Kikuchi, H. Yamamoto, J. Org. Chem. 2000, 65, 2979-2983.
8. [2b] G. Asensio, J. Gil, P. Alemán, M. Medio-Simón, Tetrahedron: Asymmetry 2001, 12, 1359-1362. Alkyllithium cleavage of silyl enol ethers or enol acetates and chiral ligands:
9. [2c] Y. Yamashita, Y. Emura, K. Odashima, K. Koga, Tetrahedron Lett. 2000, 41, 209-213. Lewis acid assisted cleavage of silyl enol ethers and chiral protic sources:
10. [2d] S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8120-8130.
11. [3a] C. Fehr, J. Galindo, Angew. Chem. Int. Ed. Engl. 1994, 33, 1888-1889.
12. [3b] Y. Nakamura, S. Takeuchi, A. Ohira, Y. Ohgo, Tetrahedron Lett. 1996, 37, 2805-2808.
13. [3c] S. Takeuchi, Y. Nakamura, Y. Ohgo, D. P. Curran, Tetrahedron Lett. 1998, 39, 8691-8694.
14. For a discussion of acidity effects in asymmetric protonation, see: E. Vedejs, A. W. Kruger, E. Suna, J. Org. Chem. 1999, 64, 7863-7870.
15. [5a] T. Ishikawa, Y. Oku, T. Tanaka, T. Kumamoto, Tetrahedron Lett. 1999, 40, 3777-3780.
16. [5b] K. Nishimura, K. Tomioka, J. Org. Chem. 2002, 67, 431-434.
17. [6a] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc. 1991, 113, 958-967.
18. [6b] M. Sujiura, T. Nakai, Angew. Chem. Int. Ed. Engl. 1997, 36, 2366-2368.
19. [6c] Review: P I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
20. [7a] J. Åhman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918-1919.
21. [7b] B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 120, 6759-6760.
22. [7c] S.-H. You, X.-L. Hou, L.-X Dai, X-Z. Zhu, Org. Lett. 2001, 3, 149-151.
23. [7d] A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1900.
24. [7e] T. Hamada, S. L. Buchwald, Org. Lett. 2002, 4, 999-1001.
25. F. Hénin, J. Muzart, J.-P. Pète, O. Piva, New J. Chem. 1991, 15, 611-613.
26. [9a] F. Hénin, J. Muzart, J-P. Pete, A. M'Boungou-M'Passi, H. Rau, Angew: Chem. Int. Ed. Engl. 1991, 30, 416-418.
27. [9b] F. Hénin, A. M'Boungou-M'Passi, J. Muzart, J.-P. Pète, Tetrahedron 1994, 50, 2849-2864.
28. J. Muzart, F. Hénin, S. Jamal Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381-389.
29. O. Roy, M. Diekmann, A. Riahi, F. Hénin, J. Muzart, Chem. Commun. 2001, 533-534 and p. 1418.
30. W. Marckwald, Ber. Dtsch. Chem. Ges. 1904, 37, 349-354.
31. H. Brunner, P. Schmidt, Eur. J. Org. Chem. 2000, 2119-2133.
32. H. Brunner, J. Müller, J. Spitzer, Monatsh. Chem. 1996, 127, 845-858.
33. [15a] H. Brunner, P. Schmidt, Z. Naturforsch., Teil B 2000, 55, 369-372.
34. [15b] H. Brunner, P. Schmidt, M. Prommesberger, Tetrahedron: Asymmetry 2000, 11, 1501-1512.
35. F. Hénin, J. Muzart, M. Nedjma, H. Rau, Monatsh. Chem. 1997, 128, 1181-1188.
36. In both cases we only observed degradation of the starting material, probably due to retro-Claisen-type reactions.
37. N. Petragnani, M. Yonashiro, Synthesis 1982, 521-578.
38. O. Piva, R. Mortezaei, F. Hénin, J. Muzart, J.-P. Pète, J. Am. Chem. Soc. 1990, 112, 9263-9272.
39. O. Piva, J.-P. Pète, Tetrahedron Lett. 1990, 31, 5157-5160.
40. A syn relative configuration has been determined for the diastereomer in slight excess (ca. 55 ± 3%) which can be compared with analogous values observed for 5a resulting from the hydride reduction of 4a: C. Alvarez Ibarra, F. Fernandez Gonzalez, M. L. Quiroga Feijoo, J. Santoro, An. Qium. 1978, 74, 449-454; C. Ivarez Ibarra, R. Pérez-Ossorio, M. L. Quiroga, M. S. Arias Pérez, M. J. Fernandez Dominguez, J. Chem. Soc., Perkin Trans. 2 1988, 101-105.
41. A syn relative configuration has been determined for the diastereomer in slight excess (ca. 55 ± 3%) which can be compared with analogous values observed for 5a resulting from the hydride reduction of 4a: C. Alvarez Ibarra, F. Fernandez Gonzalez, M. L. Quiroga Feijoo, J. Santoro, An. Qium. 1978, 74, 449-454; C. Ivarez Ibarra, R. Pérez-Ossorio, M. L. Quiroga, M. S. Arias Pérez, M. J. Fernandez Dominguez, J. Chem. Soc., Perkin Trans. 2 1988, 101-105.
42. The selectivities are greatly influenced by the nature of the support, as observed in some of our previous experiments[23] and as discussed in, for example: R. L. Augustine, Heterogenous Catalysis for the Synthetic Chemist, M. Dekker, New York, 1996, chapters 2, 3, 9.
43. S. Jamal Aboulhoda, S. Létinois, J. Wilken, I. Reiners, F. Hénin, J. Martens, J. Muzart, Tetrahedron: Asymmetry 1995, 6, 1865-1868.
44. [24a] W. Oppolzer, C. Darcel, P. Rochet, S. Rosset, J. De Brabander, Helv. Chim. Acta 1997, 80, 1319-1337.
45. [24b] T. Izawa, Y. Terao, K. Suzuki, Tetrahedron: Asymmetry 1997, 8, 2645-2648.
46. A. I. Meyers, D. R. Williams, S. White, G. W. Erickson, J. Am. Chem. Soc. 1981, 103, 3088-3093.
47. C. Fuganti, P. Grasselli, F. Spreafico, C. Zirotti, J. Org. Chem. 1984, 49, 543-546.
48. G. P. Stahly, M. R. Starrett, Chirality in Industry II, (Eds.: A. N. Collins, G. N. Sheldrake, G. Crosby), Wiley, Chichester, 1997, p. 19-40.
49. H. R. Sonawane, N. S. Bellur, J. R. Ahuja, D. G. Kulkarni, Tetrahedron: Asymmetry 1992, 3, 163-192.
50. M. Asaoka, M. Tanaka, T. Houkawa, T. Ueda, S. Sakami, H. Takei, Tetrahedron 1998, 54, 471-486.
51. J. D. Brown, Tetrahedron: Asymmetry 1992, 3, 1551-1552.
52. J. Staunton, E. Eisenbraun, Org. Synth., Coll. Vol. 1973, 5, 8-11.
53. S. Letinois, F. Hénin, J. Muzart, Tetrahedron: Asymmetry 2000, 11, 2037-2044.
54. This concept of the control of an electrophilic attack of an enolic species by the enol-bound groups was developed by Duhamel, and here we have adopted an "α' and β'" nomenclature for the enol definition (Figures 3 and 4) to avoid confusion with α- and β-positions of the carbonyl group: [33a] L. Duhamel, P. Duhamel, C. R. Acad. Sci. Paris, Série II 1995, 320, 689-694.
55. [3b] P. Duhamel, Bull. Soc. Chim. Fr. 1996, 133, 457-459.
56. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
57. Such a correlation has already been observed during the asymmetric protonation of enolates derived from Schiff bases: L. Duhamel, J.-C. Plaquevent, Bull. Soc. Chim. Fr. 1982, 11, 75-83.
58. R correspond to the rate of formation of the enantiomers, assumed to be proportional to their respective concentrations.
59. C. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 1746-1754.
60. [38a] K. Balázsik, K. Szöri, K. Felföldi, B. Török, M. Bartók, Chem. Commun. 2000, 555-556.
61. [39b] M. Von Arx, T. Mallat, A. Baiker, Tetrahedron: Asymmetry 2001, 12, 3089-3094.
62. [39a] H. Zhang, F. Xue, T. C. W. Mak, K. S. Chan, J. Org. Chem. 1996, 61, 8002-8003.
63. [39b] M. Kitamura, H. Oka, R. Noyori, Tetrahedron 1999, 55, 3605-3614.
64. M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 1473-1478.
65. M. A. Garcia-Garibay, S. Shin, C. N. Sanrame, Tetrahedron 2000, 56, 6729-6737.
66. C.-F. Yao, K.-H. Kao, J.-T. Liu, C.-M. Chu, Y. Wang, W.-C. Chen, Y.-M. Lin, W-W. Lin, M.-C. Yan, J.-Y. Liu, M.-C. Chuang, J.-L. Shiue, Tetrahedron 1998, 54, 791-822.