Enantioselective robinson-type annulation reaction catalyzed by chiral phosphoric acids

Angewandte Chemie - International Edition

Volumn 48, Issue 23, 2009, Pages 4226-4228

  Akiyama, Takahiko ^a   Katoh, Takuya ^a   Mori, Keiji ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chiral phosphoric acids; Kinetic resolution; Michael addition; Robinson type annulation

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL PHOSPHORIC ACIDS; KINETIC RESOLUTION; MICHAEL ADDITION; ROBINSON-TYPE ANNULATION;

ACIDS; ADDITION REACTIONS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY;

PHOSPHORIC ACID;

3-HYDROXYBUTANAL; ALDEHYDE; CYCLOHEXANONE DERIVATIVE; PHOSPHORIC ACID;

CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLOHEXANONES; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 70349783513     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901127     Document Type: Article

References (79)

1. R. E. Gawley, Synthesis 1976, 777-794.
2. For an example, see: J. D. White, P. Hrnciar, F. Stappenbeck, J. Org. Chem. 1999, 64, 7871-7884.
3. For proline-catalyzed reactions, see: a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493;
4. Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
5. b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621;
6. c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954;
7. d) P. H.-Y. Cheong, K. N. Houk, J. S. Warrier, S. Hanessian, Adv. Synth. Catal. 2004, 346, 1111-1115;
8. e) K. Inomata, M. Barragué, L. A. Paquette, J. Org. Chem. 2005, 70, 533-539;
9. f) F. R. Clemente, K. N. Houk, J. Am. Chem. Soc. 2005, 127, 11294-11302;
10. g) E. Lacoste, E. Vaique, M. Berlande, I. Pianet, J.-M. Vincent, Y. Landais, Eur. J. Org. Chem. 2007, 167-177.
11. For antibody-catalyzed reaction, see: G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, C. F. Barbas III, J. Am. Chem. Soc. 1997, 119, 8131-8132.
12. K. Hermann, H. Wynberg, J. Org. Chem. 1979, 44, 2238-2244.
13. H. Sasai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1994, 116, 1571-1572.
14. a) M. Nakajima, Y. Yamaguchi, S. Hashimoto, Chem. Commun. 2001, 1596-1597;
15. b) M. Nakajima, S. Yamamoto, Y. Yamaguchi, S. Nakamura, S. Hashimoto, Tetrahedron 2003, 59, 7307-7313;
16. c) C. Ogawa, K. Kizu, H. Shimizu, M. Takeuchi, S. Kobayashi, Chem. Asian J. 2006, 1, 121-124.
17. a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240-11241;
18. b) Y. Hamashima, D. Hotta, N. Umebayashi, Y. Tsuchiya, T. Suzuki, M. Sodeoka, Adv. Synth. Catal. 2005, 347, 1576-1586.
19. F. Santoro, M. Althaus, C. Bonaccorsi, S. Gischig, A. Mezzetti, Organometallics 2008, 27, 3866-3878.
20. T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem. 2003, 115, 3926-3928;
21. Angew. Chem. Int. Ed. 2003, 42, 3796-3798.
22. F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 961-964;
23. Angew. Chem. Int. Ed. 2006, 45, 947-950.
24. For reviews on phosphoric acid catalysis and related acid catalysis, see: a) S. J. Connon, Angew. Chem. 2006, 118, 4013-4016;
25. Angew. Chem. Int. Ed. 2006, 45, 3909-3912;
26. b) T. Akiyama, Chem. Rev. 2007, 107, 5744-5758;
27. c) T. Akiyama in Acid Catalysis in Modern Organic Synthesis, Vol. 1 (Eds.: H. Yamamoto, K. Ishihara), Wiley-VCH, Weinheim, 2008, pp. 62-107;
28. d) M. Terada, Chem. Commun. 2008, 4097-4112.
29. For reports from our research group, see: a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
30. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
31. b) T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 2583-2585;
32. c) T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523-1526;
33. d) T. Akiyama, Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, Synlett 2006, 141-143;
34. e) J. Itoh, T. Akiyama, K. Fuchibe, Angew. Chem. 2006, 118, 4914-4916;
35. Angew. Chem. Int. Ed. 2006, 45, 4796-4798;
36. f) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070-13071;
37. g) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764;
38. h) T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399-402;
39. i) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2008, 120, 4080-4082;
40. Angew. Chem. Int. Ed. 2008, 47, 4016-4018.
41. For selected examples of phosphoric acid catalyzed reactions, see: a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
42. b) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804-11805;
43. c) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696-15697;
44. d) R. I. Storer, D. E. Carrera, Y. Ni, D. W C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86;
45. e) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087;
46. f) M. Rueping, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679-2681;
47. Angew. Chem. Int. Ed. 2006, 45, 2617-2619;
48. g) X.-H. Chen, X.-Y Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2006, 128, 14802-14803;
49. h) M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996-7999;
50. Angew. Chem. Int. Ed. 2006, 45, 7832-7835;
51. i) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292-293;
52. j) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484-1485;
53. k) G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830-5831;
54. l) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498-7499;
55. m) M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336-10337;
56. n) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027-7030;
57. Angew. Chem. Int. Ed. 2007, 46, 6903-6906;
58. o) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606;
59. Angew. Chem. Int. Ed. 2008, 47, 593-596;
60. p) X.-H. Chen, W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652-5653;
61. q) K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2008, 130, 14452-14453;
62. r) Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem. 2008, 120, 771-774;
63. Angew. Chem. Int. Ed. 2008, 47, 759-762;
64. s) P. Jiao, D. Nakashima, H. Yamamoto, Angew. Chem. 2008, 120, 2445-2447;
65. Angew. Chem. Int. Ed. 2008, 47, 2411-2413;
66. t) M. Sickert, C. Schneider, Angew. Chem. 2008, 120, 3687-3690;
67. Angew. Chem. Int. Ed. 2008, 47, 3631-3634;
68. u) M. Terada, K. Soga, N. Momiyama, Angew. Chem. 2008, 120, 4190-4193;
69. Angew. Chem. Int. Ed. 2008, 47, 4122-4125;
70. v) D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744-5748;
71. Angew. Chem. Int. Ed. 2008, 47, 5661-5665;
72. w) X. Cheng, R. Goddard, G. Buth, B. List, Angew. Chem. 2008, 120, 5157-5159;
73. Angew. Chem. Int. Ed. 2008, 47, 5079-5081;
74. x) M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 10244-10247;
75. Angew. Chem. Int. Ed. 2008, 47, 10090-10093;
76. y) G. Li, F. R. Fronczek, J. C. Antilla, J. Am. Chem. Soc. 2008, 130, 12216-12217;
77. z) M. Rueping, A. P. Antonchick, E. Sugiono, K. Grenader, Angew. Chem. 2009, 121, 925-927;
78. Angew. Chem. Int. Ed. 2009, 48, 908-910.
79. The absolute configuration of 4a was determined by HPLC methods on a chiral stationary phase and by comparison of the retention time described in Ref. [7b]. The configurations of the other compounds were surmised by analogy.