Direct catalytic asymmetric three-component Kabachnik-fields reaction

Angewandte Chemie - International Edition

Volumn 47, Issue 27, 2008, Pages 5079-5081

  Cheng, Xu ^a   Goddard, Richard ^a   Buth, Gernot ^b   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric catalysis; Chiral phosphoric acid; Dynamic kinetic resolution; Hydrophosphonylation; Organocatalysis

Indexed keywords

ALDEHYDES; AMINES; AMINO ACIDS; CHEMICAL REACTIONS; ORGANIC ACIDS; ORGANIC COMPOUNDS; PHOSPHORIC ACID;

ASYMMETRIC CATALYSIS; CHIRAL PHOSPHORIC ACID; DYNAMIC KINETIC RESOLUTION; HYDROPHOSPHONYLATION; ORGANOCATALYSIS;

AMINATION;

ALDEHYDE; AMINE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; AMINES; CATALYSIS; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 49849086423     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801173     Document Type: Article

References (77)

1. A. B. Smith III, K. M. Yager, C. M. Taylor, J. Am. Chem. Soc. 1995, 117, 10879.
2. a) J. G. Allen, F. R. Atherton, M. J. Hall, C. H. Hassal, S. W. Holmes, R. W. Lambert, L. J. Nisbet, P. S. Ringrose, Nature 1978, 272, 56;
3. b) F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem. 1986, 29, 29.
4. E. Alonso, A. Solis, C. del Pozo, Synlett 2000, 698.
5. R. Hirschmann, A. B. Smith III, C. M. Taylor, P. A. Benkovic, S. D. Taylor, K. M. Yager, P. A. Sprengler, S. J. Benkovics, Science 1994, 265, 234.
6. For other biological applications of α-amino phosphonic acids, see: a) M. C. Allen, W. Fuhrer, B. Tuch, R. Wade, J. M. Wood, J. Med. Chem. 1989, 32, 1652;
7. b) J. Ding, M. E. Fraser, J. H. Meyer, P. A. Bartlett, M. N. G. James, J. Am. Chem. Soc. 1998, 120, 4610;
8. c) W. W. Smith, P. A. Bartlett, J. Am. Chem. Soc. 1998, 120, 4622;
9. d) J. Bird, R. C. D. Mello, G. P. Harper, D. J. Hunter, E. H. Karran, R. E. Markwell, A. J. Miles-Williams, S. S. Rahman, R. W. Ward, J. Med. Chem. 1994, 37, 158.
10. For reviews on non-catalytic variants, see: a) B. Dhawan, D. Redmore, Phosphorus Sulfur Silicon Relat. Elem. 1987, 32, 119;
11. b) V. P. Kukhar, V. A. Soloshonok, V. A. Solodenko, Phosphorus Sulfur Silicon Relat. Elem. 1994, 92, 239;
12. c) O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 1998, 9, 1279.
13. For recent examples of auxiliary-controlled asymmetric hydrophosphonylations, see: d) D. Enders, L. Tedeschi, J. W. Bats, Angew. Chem. 2000, 112, 4774;
14. Angew. Chem. Int. Ed. 2000, 39, 4605;
15. e) F. A. Davis, S. Lee, H. Yan, D. D. Titus, Org. Lett. 2001, 3, 1757.
16. For reviews on enantioselective catalytic hydrophosphonylations, see: a) H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943;
17. b) F. Palacios, C. Alonso, J. M. De Los Santos, Chem. Rev. 2005, 105, 899.
18. a) H. Sasai, S. Arai, Y. Tahara, M. Shibasaki, J. Org. Chem. 1995, 60, 6656;
19. b) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089;
20. c) S. Kobayashi, H. Kiyohara, Y. Nakamura, R. J. Matsubara, J. Am. Chem. Soc. 2004, 126, 6558.
21. G. D. Joly, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 4102.
22. T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 2583.
23. a) D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgarzani, A. Ricci, J. Org. Chem. 2006, 71, 6269;
24. b) J. Wang, L. D. Heikkinen, H. Li, L. Zu, W. Jiang, H. Xie, W. Wang, Adv. Synth. Catal. 2007, 349, 1052.
25. For a one-pot in situ sequence, see: B. Saito, H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 1978.
26. For some leading references on chiral phosphoric acid catalysis, see: a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592;
27. Angew. Chem. Int. Ed. 2004, 43, 1566;
28. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
29. c) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590;
30. Angew. Chem. Int. Ed. 2005, 44, 7424;
31. d) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696;
32. e) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
33. f) M. Rueping, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679;
34. Angew. Chem. Int. Ed. 2006, 45, 2617;
35. g) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
36. Angew. Chem. Int. Ed. 2006, 45, 4796;
37. h) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484;
38. i) Q.-X. Guo, H. Liu, C. Guo, S.-W. Luo, Y. Gu, L.-Z. Gong, J. Am. Chem. Soc. 2007, 129, 3790;
39. j) Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem. 2007, 119, 5661;
40. Angew. Chem. Int. Ed. 2007, 46, 5565;
41. k) M. J. Wanner, R. N. S. van der Haas, K. R. de Cuba, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629;
42. Angew. Chem. Int. Ed. 2007, 46, 7485;
43. l) Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem. 2008, 120, 771;
44. Angew. Chem. Int. Ed. 2008, 47, 759;
45. m) S.-M. Xu, Z. Wang, X. Zhang, X.-M. Zhang, K.-L. Ding, Angew. Chem. 2008, 120, 2882;
46. Angew. Chem. Int. Ed. 2008, 47, 2480;
47. for a review, see: n) T. Akiyama, Chem. Rev. 2007, 107, 5744.
48. S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13074.
49. For other TRIP-catalyzed reactions, see: a) T. Akiyama, Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, Synlett 2006, 141;
50. b) T. Akiyama, European Patent EP1623971, 2006;
51. c) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086;
52. d) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292-293;
53. for asymmetric counteranion-directed catalytic (ACDC) reactions involving TRIP, see: e) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
54. Angew. Chem. Int. Ed. 2006, 45, 4193;
55. f) N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368;
56. g) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498;
57. h) S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336;
58. i) G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496;
59. j) X.-W. Wang, B. List, Angew. Chem. 2008, 120, 1135;
60. Angew. Chem. Int. Ed. 2008, 47, 1119;
61. for a review on the application of TRIP in catalysis, see: k) G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, in press.
62. a) X. Qian, M. D. Shenderovich, K. E. Kövér, P. Davis, R. Horváth, T. Zalewska, H. I. Yamamura, F. Porreca, V. J. Hruby, J. Am. Chem. Soc. 1996, 118, 7280;
63. b) F. Huang, W. M. Nau, Angew. Chem. 2003, 115, 2371;
64. Angew. Chem. Int. Ed. 2003, 42, 2269;
65. c) V. J. Hruby, J. Med. Chem. 2003, 46, 4215;
66. d) B. D. Zlatopolskiy, A. de Meijere, Chem. Eur. J. 2004, 10, 4718;
67. e) T. Saito, N. Iwata, S. Tsubuki, Y. Takaki, J. Takano, S.-M. Huang, T. Suemoto, M. Higuchi, T. C. Saido, Nat. Med. 2005, 11, 434.
68. 2 benzamide, benzylamine, dibenzylamine, morpholine, and diphenylamine, which all gave no reaction. Among the anilines tested, p-anisidine gave higher enantioselectivities than p-hydroxylaniline, p-ethoxyaniline, p-phenoxyaniline, and o-methoxyaniline. We have also investigated other phospites, including diethyl-, diisopropyl-, and di(o-nitrobenzyl) phosphite and found di(3-pentyl)phosphite gave the highest enantioselectivities.
69. a) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027;
70. Angew. Chem. Int. Ed. 2007, 46, 6903;
71. b) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070;
72. c) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
73. Angew. Chem. Int. Ed. 2006, 45, 4796;
74. d) M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312;
75. Angew. Chem. Int. Ed. 2006, 45, 2254.
76. For synthetic details, see the Supporting Information.
77. CCDC-679478 (λ = 1.54178 Å) and CCDC-679479 (λ = 1.77121 Å) (4g) contain 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.