Water-more than just a green solvent: a stereoselective one-pot access to all-chiral tetrahydronaphthalenes in aqueous media

Chemistry - A European Journal

Volumn 16, Issue 12, 2010, Pages 3842-3848

  Tan, Bin ^a   Zhu, Di ^a   Zhang, Lihong ^a   Chua, Pei Juan ^a   Zeng, Xiaofei ^a   Zhong, Guofu ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Cycloaddition; Green chemistry; Michael addition; Tetra hydronaphthalenes; Water

Indexed keywords

AQUEOUS MEDIA; GREEN CHEMISTRY; GREEN SOLVENTS; MICHAEL ADDITION; MICHAEL ADDITIONS; NITRONES; ONE POT; ONE POT PROCESS; ORGANOCATALYTIC; OXAZOLIDINES; REACTION CONDITIONS; STEREO-SELECTIVE; TETRA-HYDRONAPHTHALENES; X RAY CRYSTAL STRUCTURES;

ADDITION REACTIONS; ALDEHYDES; CRYSTAL STRUCTURE; MINING; NAPHTHALENE; OLEFINS; STEREOCHEMISTRY;

CYCLOADDITION;

ALDEHYDE; ALKENE; SOLVENT; TETRALIN DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; SOLVENTS; STEREOISOMERISM; TETRAHYDRONAPHTHALENES; WATER;

EID: 77949735799     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902932     Document Type: Article

References (86)

1. a) R. T. LaLonde, M. Zhang, J. Nat. Prod. 2004, 67, 697;
2. b) A. L. Ey-berger, R. Dondapati, J. R. Porter, J. Nat Prod. 2006, 69, 1121;
3. c) Y. Wu, J. Zhao, J. Chen, C. Pan, L. Li, H. Zhang, Org. Lett. 2009, 11, 597;
4. d) H. Ge, Z. Yu, J. Zhang, J. Wu, R. Tan, J. Nat. Prod. 2009, 72, 753.
5. a) S. Archer, N. F. Albertson, L. S. Harris, A. K. Pierson, J. G. Bird, J. Med. Chem. 1964, 7, 123;
6. b) X. Yang, H. Zhai, Z. Li, Org. Lett. 2008, 10, 2457.
7. For recent reviews of organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
8. Angew. Chem. Int. Ed. 2004, 43, 5138;
9. b) C. F. Barbas III, Angew. Chem. 2007, 119, 44;
10. Angew. Chem Int. Ed. 2007, 46, 42;
11. c) S. Mukherjee, J. W. Yang, S. Hoff-mann, B. List, Chem. Rev. 2007, 107, 5471;
12. d) S. Bertelsen, M. Niel-sen, K. A. Jørgensen, Angew. Chem. 2007, 119, 7500;
13. Angew. Chem. Int. Ed. 2007, 46, 7356;
14. e) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
15. Angew. Chem. Int. Ed. 2008, 47, 4638.
16. For recent reviews of organocatalytic domino reactions, see : a) D. Enders, C. Grondai, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
17. Angew. Chem. Int. Ed. 2007, 46, 1570; for recent examples, see:
18. b) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. 2003, 115, 4365;
19. Angew. Chem. Int. Ed. 2003, 42, 4233;
20. c) Y. Yama-moto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962;
21. d) M. Marigo, T. Schulte, J. Franzen, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710;
22. e) J. W. Yang, M. T. H. Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036;
23. f) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
24. Angew. Chem. int. Ed. 2007, 46,1101;
25. g) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498;
26. h) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
27. i) N. T. Vo, R. D. Pace, M. F. O'Hara, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 404;
28. j) B. Tan, P. J. Chua, Y. Li, G. Zhong, Org. Lett. 2008, 10, 2437;
29. k) B. Tan, Z. Shi, P. J. Chua, G. Zhong, Org. Lett. 2008, 10, 3425;
30. l) B. Tan, P. J. Chua, X. Zeng, M, Lu, G. Zhong, Org. Lett. 2008, 10, 3489;
31. m) R. M, de Fi-gueiredo, R. Froelich, M. Christmann, Angew. Chem. 2008, 120, 1472;
32. Angew. Chem. Int. Ed. 2008, 47, 1450;
33. n) Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076;
34. Angew. Chem. Int. Ed. 2008, 47, 4012;
35. o) M. Lu, D. Zhu, Y. Lu, Y. Hou, B. Tan, G. Zhong, Angew. Chem. 2008, 120, 1.0341;
36. Angew. Chem. Int. Ed. 2008, 47, 10187;
37. p) B. Tan, Z. Shi, P. J. Chua, Y. Li, G. Zhong, Angew. Chem. 2009, 121, 772;
38. Angew. Chem. Int. Ed. 2009, 48, 758;
39. q) H. Jiang, P. Eisner, K. L. Jensen, A. Falcicchio, V. Marcos, K. A. Jørgensen, Angew. Chem. 2009, 121, 6976;
40. Angew. Chem. Int. Ed. 2009, 48, 6844;
41. r) L. Wu, G. Bencivenni, M. Manci-nelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332;
42. Angew. Chem Int. Ed. 2009, 48, 7196;
43. s) G. Bencivenni, L. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336;
44. Angew. Chem. Int. Ed. 2009, 48, 7200;
45. t) Q. Cai, Z. Zhao, S.-L. You, Angew. Chem. 2009, 121, 7564;
46. Angew. Chem. Int. Ed. 2009, 48, 7428.
47. a) J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahe-dron 1997, 53,13165;
48. b) K. V. Gothelf, K. A. Jø:rgensen, Chem. Rev. 1998, 98, 863;
49. c) M. S. Karatholuvhu, A. Sinclair, A. F. Newton, M. L. Alcaraz, R. A. Stockman, P. L. Fuchs, J. Am. Chem. Soc. 2006, 128, 12656;
50. d) P. Jiao, D. Nakashima, H. Yamamoto, Angew. Chem. 2008, 120, 1445;
51. Angew. Chem. Int. Ed. 2008, 47, 2411,
52. a) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737;
53. b) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393;
54. Angew. Chem. Int. Ed. 2005, 44, 1369;
55. c) S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451;
56. d) C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130;
57. Angew. Chem. Int. Ed. 2006, 45, 5984;
58. e) S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555;
59. Angew. Chem. Int. Ed. 2008, 47, 545.
60. a) D. Enders, M. R. M, Hüttl, C. Grondai, G. Raabe, Nature 2006, 441, 861;
61. b) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
62. Angew. Chem. Int. Ed. 2007, 46, 4922;
63. c) D. Enders, C. Wang, J. W. Bats, Angew. Chem. 2008, 120, 7649;
64. Angew. Chem. Int. Ed. 2008, 47, 7539;
65. d) B. C. Hong, R. Y. Nimje, M. F. Wu, A. A. Sadani, Eur. J. Org. Chem. 2008, 1449.
66. a) J. Vesely, R. Rios, I. Ibrahem, G. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2008, 14, 2693;
67. b) D. Zhu, M. Lu, L. Dai, G. Zhong, Angew. Chem. 2009, 121, 6205;
68. Angew. Chem. Int. Ed. 2009, 48, 6089.
69. The original works and review involving this type of catalyst: a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
70. Angew. Chem. Int. Ed. 2005, 44, 794;
71. b) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
72. Angew. Chem. Int. Ed. 2005, 44, 4212;
73. c) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
74. Angew. Chem. Int. Ed. 2006, 45, 7876.
75. N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barba-s III, J. Am. Chem. Soc. 2006, 128, 4966.
76. D. González-Cruz, D. Tejedor, P. de Armas, E. Q. Morales, F. García-Tellado, Chem. Commun. 2006, 2798.
77. a) P. Anastas, T. C. Williamson, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford University Press, Oxford, 1998;
78. b)G. W. V. Cave, C. L. Raston, J. L. Scott, Chem. Commun. 2001, 2159;
79. c) U. M. Lindström, Chem. Rev. 2002, 102, 2751,
80. A. Chatterjee, D. K. Maiti, P. K. Bhattacharya, Org. Lett. 2003, 5, 3967.
81. CCDC-749915 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif
82. a) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734;
83. b) Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972;
84. Angew. Chem. Int. Ed. 2006, 45, 958;
85. c) D. G. Blackmond, A. Armstrong, V. Coombe, A. Wells, Angew. Chem. 2007, 770, 3872;
86. Angew. Chem. Int. Ed. 2007, 46, 3798.