Polarity-directed one-pot asymmetric cascade reactions mediated by two catalysts in an aqueous buffer

Angewandte Chemie - International Edition

Volumn 49, Issue 13, 2010, Pages 2393-2396

  Scroggins, Steven T ^a   Chi, Yonggui ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES;

ALIPHATIC ALDEHYDES; AQUEOUS BUFFER; BIPHASIC REACTION; CASCADE REACTIONS; CROSS PRODUCT; NITROMETHANE; ONE POT; ORGANIC CATALYSTS;

CATALYSTS;

EID: 77953526823     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200902945     Document Type: Article

References (68)

1. For recent examples relevant to this study, see: a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem Soc. 2002, 124, 6798-6799;
2. b) A. Carlone, S. Cabrera, M. Marigo, K. A. Jorgensen, Angew. Chem. 2007, 119, 1119-1122;
3. Angew. Chem. Int. Ed. 2007, 46,1101-1104.
4. a) R. Ballini, R. Castagnani, M. Petřini, J. Org. Chem. 1992, 57, 2160-2162;
5. b) M. Lakshmi Kantam, P. Sreekanth, Catal. Lett. 1999, 57, 227-231;
6. c) G. Rosini in Comprehensive Organic Synthesis - Selectivity, Strategy and Efficiency in Modern Chemistry, Vol.2 (Eds.: B. M. Trost, I. Fleming), Elsevier, Oxford, 1991, pp. 321-340;
7. L. F. Tietze, U. Beifuss in Comprehensive Organic Synthesis - Selectivity, Strategy and Efficiency in Modern Chemistry, Vol.2 (Eds.: B. M. Trost, I. Fleming), Elsevier, Oxford, 1991, pp. 341-394.
8. a) S. L. Poe, M. Kobaslija, D. T. McQuade, J. Am. Chem. Soc. 2006, 128, 15586-15587;
9. b) S. L. Poe, M. Kobaslija, D. T. McQuade, J. Am Chem. Soc. 2007, 129, 9216-9221.
10. a) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894;
11. b) J. C. Vicario, D. Badia, C. Carillo, Synthesis 2007, 2065-2092;
12. c) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737;
13. d) C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. 2006, 118, 6130-6133;
14. Angew. Chem. Int Ed. 2006, 45, 5984-5987;
15. e) M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. 2006, 118, 6514-6518;
16. Angew. Chem. Int. Ed. 2006, 45, 6366-6370;
17. f) D. Enders, M. P. M. Huttl, C. Groudal, G. Raabe, Nature 2006, 441, 861-863;
18. g) D. Enders, C. Wang, J. W Bats, Angew. Chem. 2008, 120, 7649-7653;
19. Angew. Chem. Int. Ed. 2008, 47, 7539-7542;
20. h) S. Luo, X. Mi, S. Liu, H. Xu, J.-P. Cheng, Chem. Commun. 2006, 3687-3689;
21. i) M. Lu, D. Zhu, Y. Lu, Y. Hou, B. Tan, G. Zhong, Angew. Chem. 2008, 120,10341 10345;
22. Angew. Chem. Int. Ed. 2008, 47,10187-10191.
23. a) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287;
24. Angew. Chem. Int. Ed. 2005, 44, 42124215;
25. b) Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800-4802;
26. Angew. Chem Int. Ed. 2008, 47, 4722-4724;
27. c) S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555-558;
28. Angew. Chem. Int. Ed. 2008, 47, 545-548;
29. d) Y. Chi, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 56085609;
30. e) P. García-García, A Ladépêche, R. Haider, B. List, Angew. Chem. 2008, 120, 4797-4799;
31. Angew. Chem. Int. Ed. 2008, 47, 4719-4721;
32. f) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010-5013;
33. Angew. Chem. Int. Ed. 2007, 46, 4922-4925.
34. We use the term "homo" to refer to cascade reactions incorporating the same aldehyde in both steps. The term "cross" refers to reactions incorporating different aldehydes in each step.
35. a) M. T. Hechavarria Fonseca, B. List, Angew. Chem. 2004, 116, 4048-4050;
36. Angew. Chem. Int. Ed. 2004, 43, 3958-3960;
37. b) G- L. Zhao, J. Veselý, J. Sun, K. E. Christensen, C. Bonneau, A. Cordova, Adv. Synth. Catal 2008, 350, 657-661.
38. a) M. Gruttadauria, F. Giacalone, R. Noto, Adv. Synth. Catal. 2009, 351, 33-57;
39. b) J. Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. 2009, 121, 4352-4362;
40. Angew. Chem. Int. Ed 2009, 48, 4288-4297;
41. c) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734-735;
42. d) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc 2006, 128, 4966-4967;
43. e)Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972-975;
44. Angew. Chem. Int. Ed. 2006, 45, 958-961;
45. f) Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653-5655;
46. Angew. Chem Int. Ed. 2006, 45, 5527-5529;
47. g) A. Córdova, W. Notz, C. F. Barbas III, Chem. Commun. 2002, 3024-3025;
48. h) Z. Jiang, Z. Liang, X. Wu, Y. Lu, Chem. Commun. 2006, 2801-2803;
49. i) B. Tan, Z. Shi, P. J. Chua, Y. Li, G. Zhong,Angew. Chem. 2009, 121, 112-775;
50. Angew. Chem. Int. Ed. 2009, 48, 758-761;
51. j) Y. Chi, S. T. Scroggins, E. Boz, J. M. J. Fréchet, J. Am. Chem. Soc 2008, 130, 17287-17289.
52. a) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042-8046;
53. Angew. Chem. Int. Ed. 2006, 45, 7876-7880;
54. b) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jorgensen, Angew. Chem. 2005, 117, 804-807;
55. Angew. Chem. Int. Ed. 2005, 44, 794-797;
56. c) Y.Chi, S. H. Gellman, Org. Lett. 2005, 7, 4253-4256.
57. a) D. G. Blackmond, A. Armstrong, V. Coombe, A. Wells, Angew. Chem. 2007, 119, 3872-3874;
58. Angew. Chem. Int Ed. 2007, 46, 3798-3800;
59. b) A. P. Brogan, T.J. Dickerson, K. D.Janda, Angew. Chem. 2006, 118, 8278-8280;
60. Angew. Chem. Int.Ed. 2006, 45, 8100-8102;
61. c) Y. Hayashi, Angew. Chem. 2006, 118, 8281-8282;
62. Angew. Chem. Int. Ed. 2006, 45, 8103-8104.
63. Y. Chi, T.J. Peelen, S. H. Gellman, Org. Lett. 2005, 7, 34693472.
64. R. Benigni, L. Conti, R. Crebelli, A. Rodomonte, M. R. Vari, Environ. Mol. Mutagen. 2005, 46, 268-280.
65. a) J-L. Reymond, Y. Chen, J. Org. Chem. 1995, 60, 6970-6979;
66. b) T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 220-3221.
67. H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W Wang, Org. Lett. 2007, 9, 1833-1835.
68. B. Helms, J. M.J. Fréchet, Adv. Synth. Catal. 2006, 348, 11251148.