Enantioselective rhodium-catalyzed addition of arylboronic acids to α-ketoesters

Angewandte Chemie - International Edition

Volumn 47, Issue 23, 2008, Pages 4351-4353

  Duan, Hai Feng ^a   Xie, Jian Hua ^a   Qiao, Xiang Chen ^a   Wang, Li Xin ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

ketoester; Alcohols; Asymmetric catalysis; Boronic acids; Rhodium

Indexed keywords

ACIDS; ESTERS;

ALCOHOLS; ARYL BORONIC ACIDS; ASYMMETRIC ADDITION; ASYMMETRIC CATALYSIS; BORONIC ACIDS; ENANTIOSELECTIVE; KETOESTERS; RHODIUM CATALYSIS; RHODIUM-CATALYZED;

RHODIUM;

BORONIC ACID DERIVATIVE; KETONE; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; TECHNIQUE;

BORONIC ACIDS; CATALYSIS; KETONES; METHODS; RHODIUM; STEREOISOMERISM;

EID: 46749096379     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800423     Document Type: Article

References (55)

1. st ed., Springer, Berlin, 1999;
2. b) L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757;
3. c) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169;
4. d) S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763;
5. e) C. Garcia, V. S. Martin, Curr. Org. Chem. 2006, 10, 1849;
6. f) O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873.
7. For recent examples, see g) F. Schmidt, J. Rudolph, C. Bolm, Adv. Synth. Catal. 2007, 349, 703;
8. h) J. Siewert, R. Sandmann, P. von Zezschwith, Angew. Chem. 2007, 119, 7252;
9. Angew. Chem. Int. Ed. 2007, 46, 7122.
10. a) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475;
11. Angew. Chem. Int. Ed. 1998, 37, 3279;
12. b) T. Fuchen, J. Rudolph, C. Bolm, Synthesis 2005, 429;
13. c) H.-F. Duan, J.-H. Xie, W.-J. Shi, Q. Zhang, Q.-L. Zhou, Org. Lett. 2006, 8, 1479;
14. d) R. B. C. Jagt, P. Y. Toullec, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Org. Biomol. Chem. 2006, 4, 773;
15. e) D. Tomita, M. Kanai, M. Shibasaki, Chem. Asian J. 2006, 1, 161;
16. f) K. Suzuki, K, Kondo, T. Aoyama, Synthesis 2006, 8, 1360;
17. g) R. B. C. Jagt, P. Y. Toullec, E. P. Schudde, J. G. De Vries, B. L. Feringa, A. J. Minnaard, J. Comb. Chem. 2007, 9, 407.
18. a) D. J. Weix, Y. Shi, J. A. Ellman, J. Am. Chem. Soc. 2005, 127, 1092;
19. b) H.-F. Duan, J.-H. Xie, L.-X. Wang, Q.-L. Zhou, Org. Lett. 2006, 8, 2567;
20. c) R. B. C. Jagt, P. Y. Toullec, D. Geerdink, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Angew. Chem. 2006, 118, 2855;
21. Angew. Chem. Int. Ed. 2006, 45, 2789;
22. d) M. A. Beenen, D. J. Weix, J. A. Ellman, J. Am. Chem. Soc. 2006, 128, 6304;
23. e) H. Nakagawa, J. C. Rech, R. W. Sindelar, J. A. Ellman, Org. Lett. 2007, 9, 5155;
24. f) Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2007, 129, 5336.
25. R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. 2006, 118, 3431;
26. Angew. Chem. Int. Ed. 2006, 45, 3353.
27. P. Y. Toullec, R. B. C. Jagt, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2006, 8, 2715.
28. S. L. X. Martina, R. B. C. Jagt, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Chem. Commun. 2006, 4093.
29. G. Liu, X. Lu, J. Am. Chem. Soc. 2006, 128, 16504.
30. For catalytic asymmetric addition of organozinc reagents to α-ketoesters, see: a) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12668;
31. b) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5647;
32. Angew. Chem. Int. Ed. 2003, 42, 5489;
33. c) L. C. Wieland, H. Deng, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 15453;
34. d) G. Blay, I. Fernandez, A. Marco-Aleixandre, J. R. Pedro, Org. Lett. 2006, 8, 1287.
35. For nonasymmetric addition of arylboronic acids to α-ketoesters, see: e) P. He, Y. Lu, C.-G. Dong, Q.-S. Hu, Org. Lett. 2007, 9, 343;
36. f) S. Miyamura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 2255;
37. g) G. R. Ganci, J. D. Chisholm, Tetrahedron Lett. 2007, 48, 8266.
38. a) D. O. Kiesewetter, J. V. Silverton, W. C. Eckelman, J. Med. Chem. 1995, 38, 1711;
39. b) D. O. Kiesewetter, R. E. Carson, E. M. Jagoda, C. J. Endres, M. G. Der, P. Herscovitch, W. C. Eckelman, Bioorg. Med. Chem. 1997, 5, 1555;
40. c) M. B. Skaddan, M. R. Kilbourn, S. E. Snyder, P. S. Sherman, T. J. Desmond, K. A. Frey, J. Med. Chem. 2000, 43, 4552;
41. d) J. Selent, W. Brandt, D. Pamperin, B. Goeber, Bioorg. Med. Chem. 2006, 14, 1729.
42. For reviews: see a) H. Gröger, Adv. Synth. Catal. 2001, 343, 547;
43. b) D. J. Ramón, M. Yus, Angew. Chem. 2004, 116, 286;
44. Angew. Chem. Int. Ed. 2004, 43, 284.
45. For recent example, see c) Y.-T. Hong, C.-W. Cho, E. Skucas, M. J. Krische, Org. Lett. 2007, 9, 3745.
46. 2] was the best choice for the precatalyst becasue it led to high yields.
47. The reaction was incomplete and the yield was very low in the absence of LiF.
48. a) S. W. Wright, D. L. Hageman, L. D. McClure, J. Org. Chem. 1994, 59, 6095;
49. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147;
50. c) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020.
51. A. I. Meyers, J. Slade, J. Org. Chem. 1980, 45, 2912.
52. a) C. Bugno, S. M. Colombani, P. Dapporto, G. Garelli, P. Giorgi, A. Subissi, L, Turbanti, Chirality 1997, 9, 713;
53. b) E. R. Atkinson, D. D. McRitchi, L. F. Schoer, J. Med. Chem. 1977, 20, 1612.
54. a) M. Scholl, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 1425;
55. b) M. E. Vargas-Díaz, L. C. García, P. Velàzquez, J. Tamariz, P. J. Nathan, L. G. Zepeda, Tetrahedron: Asymmetry 2003, 14, 3225.