Chiral chalcogen peptides as ligands for the catalytic enantioselective aryl transfer reaction to aldehydes

European Journal of Organic Chemistry

Volumn , Issue 19, 2010, Pages 3574-3578

  Schwab, Ricardo S ^a   Soares, Letiere C ^a   Dornelles, Luciano ^a   Rodrigues, Oscar E D ^a   Paixao, Márcio W ^b   Godoi, Marcelo ^c   Braga, Antonio L ^c  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^c FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Arylboronic acids; Asymmetric synthesis; Chalcogen peptides; Diarylmethanols; Organozinc reagents; Selenium

Indexed keywords

EID: 77953824590     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000237     Document Type: Article

References (64)

1. a) D. A. Evans, Science 1988, 240, 420-126;
2. b) R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69;
3. c) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188;
4. d) K. Soai, T. Shibata, in: E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer-Verlag, Berlin, 1999, pp. 1-911.
5. For a recent review on catalytic enantioselective arylation, see: a) F. Schmidt, R. T. Stemmler, J. Rudolph, C. Bolm, Chem. Soc. Rev. 2006, 35, 454-470;
6. b) M. W. Paixão, A. L. Braga, D. S. Lüdtke, J. Braz. Chem. Soc. 2008, 19, 813-830.
7. a) C. Bolm, N. Hermanns, J. P. Hildebrand, K. Muftiz, Angew. Chem. Int. Ed. 2001, 40, 3284-3308;
8. b) V. Dimitrovi, K. Kostova, Lett. Org. Chem. 2006, 3, 176-182;
9. c) J. G. Kim, P. J. Walsh, Angew. Chem. Int. Ed. 2006, 45, 4175-4178;
10. d) L. Salvi, J. G. Kim, P. J. Walsh, J. Am. Chem. Soc. 2009, 131, 12483-12493.
11. a) K. Meguro, M. Aizawa, T. Solida, Y. Kawamatsu, A. Nagaoka, Chem. Pharm. Bull. 1985, 33, 3787-3797;
12. b) F. Toda, K. Tanaka, K. Koshiro, Tetrahedron: Asymmetry 1991, 2, 873-874;
13. c) S. Stanchev, R. Rakovska, N. Berova, G. Snatzke, Tetrahedron: Asymmetry 1995, 6, 183-198;
14. d) M. Botta, V. Summa, F. Corelli, G. Di Pietro, P. Lombardi, Tetrahedron: Asymmetry 1996, 7, 1263-1266;
15. e) K. Yamamoto, K. Tsurumi, F. Sakurai, K. Kondo, T. Aoyama, Synthesis 2008, 3585-3590.
16. For B/Zn exchange reactions, see: a) M. Srebnik, Tetrahedron Lett. 1991, 32, 2449-2452;
17. b) W. Oppolzer, R. N. Radinov, Helv. Chim. Acta 1992, 75, 170-173;
18. c) W. Oppolzer, R. N. Radinov, J. Am. Chem. Soc. 1993, 115, 1593-1594;
19. d) F. Langer, L. Schwink, A. Devasagayaraj, R.-Y. Chavant, P. Knochel, J. Org. Chem. 1996, 61, 8229-8243;
20. e) A. Boudier, L. O. Bromm, M. Lotz, P. Knochel, Angew. Chem. Int. Ed. 2000, 39, 4414-4435;
21. f) O. Pietro, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2003, 14, 1955-1957;
22. g) V. J. Forrat, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2005, 16, 3341-3344;
23. h) V. J. Forrat, O. Pietro, D. Ramón, M. Yus, Chem. Eur. J. 2006, 12, 4431-4445;
24. i) V. J. Forrat, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2006, 17, 2054-2058;
25. j) V. J. Forrat, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2008, 19, 537-541;
26. k) X. Huang, L. Wu, J. Xu, L. Zong, H. Hu, Y. Cheng, Tetrahedron Lett. 2008, 49, 6823-6826;
27. l) V. J. Forrat, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2009, 20, 65-67.
28. a) C. Bolm, J. Rudolph, F. Schmidt, Synthesis 2005, 840-842;
29. b) S. Ozçubukçu, F. Schmidt, C. BoIm, Org. Lett. 2005, 7, 1407-1409;
30. c) A. L. Braga, D. S. Lüdtke, F. Vargas, M. W. Paixão, Chem. Commun. 2005, 2512-2514;
31. d) A. L. Braga, D. S. Lüdtke, F. Vargas, P. H. Schneider, M. W. Paixão, A. Schneider, L. A. Wessjohann, Tetrahedron Lett. 2005, 46, 7827-7830;
32. e) X. y. Liu, X. y. Wu, Z. Chai, Y. y. Wu, G. Zhao, S. z. Zhu, J. Org. Chem. 2005, 70, 7432-7435;
33. f) S. Dahmen, M. Lormann, Org. Lett. 2005, 7, 4597-4600;
34. g) J. G. Kim, P. J. Walsh, Angew. Chem. Int. Ed. 2006, 45, 4175-4178;
35. h) G. Lu, F. Y. Kwong, J.-W. Ruan, Y-M. Li, A. S. C. Chan, Chem. Eur. J. 2006, 12, 4115-4120;
36. i) M. W. Paixão, M. de Godoi, C. R. B. Rhoden, B. Westermann, L. A. Wessjohann, D. S. Lüdtke, A. L. Braga, J. Mol. Cat. A: Chem. 2007, 261, 120-124;
37. j) A. L. Braga, M. W. Paixão, B. Westermann, P. H. Schneider, L. A. Wessjohann, J. Org. Chem. 2008, 73, 2879-2882;
38. k) J. Ruan, G. Lu, L. Xu, Y.-M. Li, A. S. C. Chan, Adv. Synth. Catal. 2008, 350, 76-84;
39. l) M.-C. Wang, Q.-J. Zhang, W-X. Zhao, X.-D. Wang, X. Ding, T.-T. Jing, M.-P. Song, J. Org. Chem. 2008, 73, 168-176;
40. m) C. Liu, Z.-L. Guo, J.Weng, G. Lu, A. S. C. Chan, Chirality 2010, 22, 159-164.
41. a) R.-Y. Wu, H.-L. Wu, B.-J. Uang, J. Org. Chem. 2006, 71, 833-835;
42. b) A. L. Braga, P. Milani, F. Vargas, M. W. Paixão, J. A. Sehnem, Tetrahedron: Asymmetry 2006, 17, 2793-2797;
43. c) Z. Chai, X.-Y. Liu, X.-Y. Wu, G. Zhao, Tetrahedron: Asymmetry 2006, 17, 2442-2447;
44. d) M.-J. Jin, S. M. Sarkar, D.-H. Lee, H. Qiu, Org. Lett. 2008, 10, 1235-1237.
45. C. Bolm, M. Kesselgruber, A. Grenz, N. Hermmanns, J. P. Hildebrand, New J. Chem. 2001, 25, 13-15.
46. a) E. R. Jarvo, S. J.Miller, Tetrahedron 2002, 58, 2481-2495;
47. b) E. A. C. Davie, S. M. Mennen, Y. Xu, S. J. Miller, Chem. Rev. 2007, 107, 5759-5812;
48. c) R. S. Schwab, F. Z. Galetto, J. B. Azeredo, A. L. Braga, D. S. Lüdtke, M. W. Paixão, Tetrahedron Lett. 2008, 49, 5094-5097.
49. For selected examples, see: a) H.-Q. Cai, C. Chen, L. Liu, JM. Ni, R. Wang, J. Mol. Cat. A: Chem. 2006, 253, 86-91;
50. b) C. L. Wieland, H. Deng, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 15453-15456;
51. c) C. M. Sprout, M. L. Richmond, C., T Seto, J. Org. Chem. 2005, 70, 7408-7417.
52. For selected examples, see: a) A. L. Braga, D.S. Lüdtke, F. Vargas, R. C. Braga, Synlett 2006, 1453-1466;
53. b) A. L. Braga, D. S. Lüdtke, F. Vargas, Curr. Org. Chem. 2006, 10, 1921-1938;
54. c) A. L. Braga, M. W. Paixão, D. S. Lüdtke, C. C. Silveira, O. E. D. Rodrigues, Org. Lett. 2003, 5, 2635-2638;
55. d) A. L. Braga, P. Milani, M. W. Paixão, G. Zeni, O. E. D. Rodrigues, E. F. Alves, Chem. Commun. 2004, 2488-2489;
56. e) P. H. Schneider, H. S. Schrekker, C. C. Silveira, L. A. Wessjohann, A. L. Braga, Eur. J. Org. Chem. 2004, 2715-2722;
57. f) A. L. Braga, D. S. Lüdtke, E. E. Alberto, J. A. Sehnem, Tetrahedron 2005, 61, 11664-11671;
58. g) A. L. Braga, J. A. Sehnem, F. Vargas, R. C. Braga, J. Org. Chem. 2005, 70, 9021-9024.
59. A. L. Braga, O. E. D. Rodrigues, M. W. Paixão, H. R. Appelt, C. C. Silveira, D. P. Bottega, Synthesis 2002, 2338-2340.
60. J. Rudolph, N. Hermanns, C. Bolm, J. Org. Chem. 2004, 69, 3997-4000.
61. C. Jimeno, S. Sayalero, T Fjermestad, G. Colet, F. Maseras, M. A. Pericas, Angew. Chem. Int. Ed. 2008, 47, 1098-1101.
62. a) C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851;
63. b) F. Schimdt, J. Rudolph, C. Bolm, Adv. Synth. Catal. 2007, 349, 703-708.
64. K. Yamamoto, K. Tsurumi, F. Sakurai, K. Kondo, T. Aoyama, Synthesis 2008, 3585-3590.