Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: Highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones

Angewandte Chemie - International Edition

Volumn 49, Issue 49, 2010, Pages 9460-9464

  Guo, Qunsheng ^a   Bhanushali, Mayur ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

aldol reaction; enantioselectivity; ketones; organocatalysis; reaction mechanisms

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC ALDOL REACTIONS; CARBONYL COMPOUNDS; ENAMINES; ENANTIOSELECTIVE SYNTHESIS; ENOLATES; ORGANOCATALYSIS; REACTION MECHANISM;

CARBONYLATION; CATALYSIS; CONDENSATION REACTIONS; ENANTIOSELECTIVITY; KETONES; RATE CONSTANTS; REACTION KINETICS; THIOUREAS; UREA;

SYNTHESIS (CHEMICAL);

3 HYDROXYINDOLIN 2 ONE; 3-HYDROXYINDOLIN-2-ONE; INDOLE DERIVATIVE; KETONE; QUINIDINE; THIOUREA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDOLES; KETONES; MOLECULAR STRUCTURE; QUINIDINE; STEREOISOMERISM; THIOUREA;

EID: 78650157659     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004161     Document Type: Article

References (65)

1. T. Mukaiyama, Org. React. 1982, 28, 203-331
2. Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004.
3. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
4. For selected reviews, see
5. B. List, Acc. Chem. Res. 2004, 37, 548-557
6. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580-591
7. B. List, Tetrahedron 2002, 58, 5573-5590
8. H. Pellissier, Tetrahedron 2007, 63, 9267-9331.
9. C. A. Wurtz, J. Prakt. Chem. 1872, 5, 457-464.
10. For examples of tertiary amine-mediated diastereoselective aldol reactions involving enolates of activated ketones, see
11. M. Markert, M. Mulzer, B. Schetter, R. Mahrwald, J. Am. Chem. Soc. 2007, 129, 7258-7259
12. T. K. M. Shing, H. M. Cheng, Org. Lett. 2008, 10, 4137-4139.
13. For examples of chiral Brønsted base-catalyzed aldol reactions, see
14. J. Paradowska, M. Rogozinńska, J. Mlynarski, Tetrahedron Lett. 2009, 50, 1639-1641
15. L. Li, E. G. Klauber, D. Seidel, J. Am. Chem. Soc. 2008, 130, 12248-12249
16. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286-6287. For reviews, see
17. B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601
18. C. Palomo, M. Oiarbide, J. M. García, Chem. Soc. Rev. 2004, 33, 65-75.
19. For an example of organocatalyzed enantioselective aldol reaction involving an enol intermediate, see:, G. Pousse; F. Le Cavelier, L. Humphreys, J. Rouden, J. Blanchet, Org. Lett. 2010, 12, 3582-3585
20. F. Le Cavelier, L. Humphreys, J. Rouden, J. Blanchet, Org. Lett. 2010, 12, 3582-3585.
21. S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442-7443
22. R. Dodda, C.-G. Zhao, Org. Lett. 2006, 8, 4911-4914
23. S. Samanta, S. Perera, C.-G. Zhao, J. Org. Chem. 2010, 75, 1101-1106
24. C.-G. Zhao, R. Dodda, Synlett 2007, 1605-1609.
25. 3, see
26. S. J. Garden, R. B. da Silva, A. C. Pinto, Tetrahedron 2002, 58, 8399-8412
27. S. J. Garden, J. C. Torres, A. A. Ferreira, R. B. da Silva, A. C. Pinto, Tetrahedron Lett. 1997, 38, 1501-1504
28. F. Braude, H. G. Lindwall, J. Am. Chem. Soc. 1933, 55, 325-327.
29. For examples, see
30. M. Raj, N. Veerasamy, V. K. Singh, Tetrahedron Lett. 2010, 51, 2157-2159
31. S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J. 2008, 14, 8079-8081
32. A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluhackova, P. Kocovsky, Org. Lett. 2007, 9, 5473-5476
33. J.-R. Chen, X.-P. Liu, X.-Y. Zhu, L. Li, Y.-F. Qiao, J.-M. Zhang, W.-J. Xiao, Tetrahedron 2007, 63, 10437-10444
34. G. Chen, Y. Wang, H. He, S. Gao, X. Yang, X. Hao, Heterocycles 2006, 68, 2327-2333
35. G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem. 2005, 70, 7418-7421
36. F. Xue, S. Zhang, L. Liu, W. Duan, W. Wang, Chem. Asian J. 2009, 4, 1664-1667
37. W.-B. Chen, X.-L. Du, L.-F. Cun, X.-M. Zhang, W.-C. Yuan, Tetrahedron 2010, 66, 1441-1446
38. N. Hara, S. Nakamura, N. Shibata, T. Toru, Adv. Synth. Catal. 2010, 352, 1621-1624
39. T. Itoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2009, 11, 3854-3857
40. G. Angelici, R. J. Corrêa, S. J. Garden, C. Tomasini, Tetrahedron Lett. 2009, 50, 814-817.
41. For examples, see
42. R. R. Goehring, Y. P. Sachdeva, J. S. Pisipati, M. C. Sleevi, J. F. Wolfe, J. Am. Chem. Soc. 1985, 107, 435-443
43. R. B. Labroo, L. A. Cohen, J. Org. Chem. 1990, 55, 4901-4904
44. H. B. Rasmussen, J. K. MacLeod, J. Nat. Prod. 1997, 60, 1152-1154
45. J. Jimenez, U. Huber, R. Moore, G. Patterson, J. Nat. Prod. 1999, 62, 569-572
46. T. Tokunaga, W. E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, R. Nagata, J. Med. Chem. 2001, 44, 4641-4649
47. T. Tokunaga, W. E. Hume, J. Nagamine, T. Kawamura, M. Taiji, R. Nagata, Bioorg. Med. Chem. Lett. 2005, 15, 1789-1792.
48. For selected reviews on thiourea catalysis, see
49. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296
50. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299- 4306
51. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
52. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
53. S. J. Connon, Chem. Eur. J. 2006, 12, 5418-5427
54. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743.
55. The ee value of 12 a could be improved to 89 % by further dropping the reaction temperature to -15 °C, but the yield obtained was impractical.
56. For examples of organocatalyzed aldol reaction of aryl methyl ketones with a proline-derived tetrazole, see
57. H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017-2020
58. Angew. Chem. Int. Ed. 2004, 43, 1983-1986; with a pyrrolidine sulfonamide, see
59. K. Mei, S. Zhang, S. He, P. Li, M. Jin, F. Xue, G. Luo, H. Zhang, L. Song, W. Duan, W. Wang, Tetrahedron Lett. 2008, 49, 2681-2684; with proline, see
60. C.-G. Zhao, R. Dodda, Synthesis 2006, 3238-3242.
61. 1H NMR data, see:, K. Miura, T. Nakagawa, A. Hosomi, J. Am. Chem. Soc. 2002, 124, 536-537.
62. For an example that leads to the syn aldol product, see:, T. Kano, Y. Yamaguchi, Y. Tanaka, K. Maruoka, Angew. Chem. 2007, 119, 1768-1770
63. Angew. Chem. Int. Ed. 2007, 46, 1738-1740.
64. H. V. Erkizan, Y. Kong, M. Merchant, S. Schlottmann, J. S. Barber-Rotenberg, L. Yuan, O. D. Abaan, T.-H. Chou, S. Dakshanamurthy, M. L. Brown, A. Üren, J. A. Toretsky, Nat. Med. 2009, 15, 750-757.
65. The ee value may be increased to >99.5 % ee by a single recrystallization with a 65 % recovery.