Asymmetric amplification using chiral cocrystals formed from achiral organic molecules by asymmetric autocatalysis

Angewandte Chemie - International Edition

Volumn 44, Issue 18, 2005, Pages 2774-2777

  Kawasaki, Tsuneomi ^a   Jo, Kazumichi ^a   Igarashi, Hirotaka ^a   Sato, Itaru ^a   Nagano, Masaki ^b   Koshima, Hideko ^b   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b EHIME UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Autocatalysis; Chirality; Cocrystals; Zinc

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; MOLECULAR CRYSTALS; REACTION KINETICS;

ASYMMETRIC AMPLIFICATION; CHIRAL COCRYSTALS; ENANTIOSELECTIVE ADDITION; PHENANTHRIDINE;

ADDITION REACTIONS;

ALKENE; PYRIMIDINE; PYRIMIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION; STEREOISOMERISM;

ALKENES; CATALYSIS; CRYSTALLIZATION; MOLECULAR STRUCTURE; PYRIMIDINES; STEREOISOMERISM;

EID: 18844432602     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462963     Document Type: Article

References (76)

1. a) B. L. Feringa, R. A. van Delden, Angew. Chem. 1999, 111, 3624-3645;
2. Angew. Chem. Int. Ed. 1999, 38, 3418-3438;
3. b) K. Mislow, Collect. Czech. Chem. Commun. 2003, 68, 849-864;
4. c) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127;
5. Angew. Chem. Int. Ed. 1998, 37, 2923-2959;
6. d) A. Eschenmoser, Science 1999, 284, 2118-2124;
7. e) H. Zepik, E. Shavit, M. Tang, T. R. Jensen, K. Kjaer, G. Bolbach, L. Leiserowitz, I. Weissbuch, M. Lahav, Science 2002, 295, 1266-1269;
8. f) M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3329-3345;
9. Angew. Chem. Int. Ed. 1999, 38, 3139-3154;
10. g) W. A. Bonner, Origins Life Evol. Biosphere 1995, 25, 175-190;
11. h) D. K. Kondepudi, K. Asakura, Acc. Chem. Res. 2001, 34, 946-954;
12. i) J. S. Siegel, Chirality 1998, 10, 24-27;
13. j) S. Mason, Chem. Soc. Rev. 1988, 17, 347-359;
14. k) L. Keszthelyi, Q. Rev. Biophys. 1995, 28, 473-507;
15. l) V. Avetisov, V. Goldanskii, Proc. Natl. Acad. Sci. USA 1996, 93, 11435-11442;
16. m) M. Avalos, R. Babiano, P. Cintas, J. L. Jimenez, J. C. Palacios, Tetrahedron: Asymmetry 2000, 11, 2845-2874.
17. a) J. Jacques, A. Collet, S. M. Wilen, Enantiomers, Racemates, and Resolutions, Wiley, New York, 1981, p. 14;
18. b) B. S. Green, M. Lahav, D. Rabinovich, Acc. Chem. Res. 1979, 12, 191-197;
19. for chiral crystallization of inorganic sodium chlorate, see c) R. M. Pagni, R. N. Compton, Cryst. Growth Des. 2002, 2, 249-253;
20. d) D. K. Kondepudi, R. J. Kaufman, N. Singh, Science 1990, 250, 975-977.
21. M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689.
22. a) H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato, M. Kiguchi, Tetrahedron Lett. 1997, 38, 5009-5012;
23. b) H. Koshima, S. Honke, F. Fujita, J. Org. Chem. 1999, 64, 3916-3921;
24. c) H. Koshima, M. Miyauchi, M. Shiro, Supramol. Chem. 2001, 13, 137-142;
25. d) H. Koshima, M. Nagano, T. Asahi, J. Am. Chem. Soc., 2005, 127, 2455-2463.
26. Reviews: a) M. Hasegawa, Chem. Rev. 1983, 83, 507-518;
27. b) V. Ramamurthy, K. Vebkatesan, Chem. Rev. 1987, 87, 433-481;
28. c) J. R. Scheffer, M. Garcia-Garibay, Photochemistry on Solid Surface (Eds.: M. Anpo, T. Matsuura), Elsevier, Amsterdam 1989, chap. 9, p. 501;
29. d) K.-L. Ding, Y. Wang, Y.-J. Wu, H. Matsuura, Youji Huaxue 1996, 16, 1;
30. e) H. Koshima, T. Matsuura, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1998, 56, 268-279;
31. f) H. Koshima, T. Matsuura, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1998, 56, 466-477.
32. a) M. D. Cohen, G. M. J. Schmidt, J. Chem. Soc. 1964, 1996-2000;
33. b) K. Penzien, G. M. Schmidt, Angew. Chem. 1969, 81, 628;
34. Angew. Chem. Int. Ed. Engl. 1969, 8, 608-609;
35. c) A. Elgavi, B. S. Green, G. M. J. Schmidt, J. Am. Chem. Soc. 1973, 95, 2058-2059.
36. a) L. Addadi, M. Lahav, J. Am. Chem. Soc. 1978, 100, 2838-2844;
37. c) L. Addadi, M. Lahav, J. Am. Chem. Soc. 1979, 101, 2152-2156;
38. d) S. V. Evans, M. Garcia-Garibay, N. Omkaram, J. R. Scheffer, J. Trotter, F. Wireko, J. Am. Chem. Soc. 1986, 108, 5648-5650;
39. e) M. Hasegawa, C.-M. Chung, N. Murro, Y, Maekawa, J. Am. Chem. Soc. 1990, 112, 5676-5677;
40. f) A. L. Roughton, M. Muneer, M. Demuth, J. Am. Chem. Soc. 1993, 115, 2085-2087;
41. g) F. Toda, K. Tanaka, Supramol. Chem. 1994, 3, 87-88;
42. h) T. Suzuki, T. Fukushima, Y. Yamashita, T. Miyashi, J. Am. Chem. Soc. 1994, 116, 2793-2803;
43. i) H. Koshima, K.-L. Ding, Y. Chisaka, T. Matsuura, J. Am. Chem. Soc. 1996, 118, 12 059-12 065.
44. Reviews: a) K. Soai, T. Shibata, I. Sato, Acc. Chem. Res. 2000, 33, 382-390;
45. b) K. Soai, I. Sato, T. Shibata, Chem. Rec. 2001, 1, 321-332;
46. c) C. Bolm, F. Bienewald, A. Seger, Angew. Chem. 1996, 108, 1767-1769;
47. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657-1659;
48. d) M. Avalos, R. Babiano, P. Cintas, J. L. Jiménez, J. C. Palacios, Chem. Commun. 2000, 887-892;
49. e) H. Buschmann, R. Thede, D. Heller, Angew. Chem. 2000, 112, 4197-4200;
50. Angew. Chem. Int. Ed. 2000, 39, 4033-4036;
51. f) M. H. Todd, Chem. Soc. Rev. 2002, 31, 211-222;
52. g) K. Soai, T. Shibata, I. Sato, Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073;
53. h) K. Mikami, M. Yamanaka, Chem. Rev. 2003, 103, 3369-3400.
54. a) K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768;
55. b) T. Shibata, T. Hayase, J. Yamamoto, K. Soai, Tetrahedron: Asymmetry 1997, 8, 1717-1719;
56. c) T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai, K. Soai, J. Am. Chem. Soc. 1998, 120, 12 157-12 158;
57. d) K. Soai, S. Osanai, K. Kadowaki, S. Yonekubo, T. Shibata, I. Sato, J. Am. Chem. Soc. 1999, 121, 11 235-11 236;
58. e) I. Sato, D. Omiya, T. Saito, K. Soai, J. Am. Chem. Soc. 2000, 122, 11 739-11 740;
59. f) I. Sato, R. Yamashima, K. Kadowaki, J. Yamamoto, T. Shibata, K. Soai, Angew. Chem. 2001, 113, 1130-1132;
60. Angew. Chem. Int. Ed. 2001, 40, 1096-1098;
61. g) I. Sato, H. Urabe, S. Ishiguro, T. Shibata, Angew. Chem. 2003, 115, 329-331;
62. Angew. Chem. Int. Ed. 2003, 42, 315-317;
63. h) I. Sato, K. Kadowaki, Y. Ohgo, K. Soai, J. Mol. Catal. A 2004, 216, 209-214;
64. i) I. Sato, T. Nakao, R. Sugie, T. Kawasaki, K. Soai, Synthesis 2004, 1419-1428;
65. j) I. Sato, M. Shimizu, T. Kawasaki, K. Soai, Bull. Chem. Soc. Jpn. 2004, 77, 1587-1588;
66. k) I. Sato, R. Sugie, Y. Matsueda, Y. Furumura, K. Soai, Angew. Chem. 2004, 116, 4590-4592;
67. Angew. Chem. Int. Ed. 2004, 43, 4490-4492;
68. l) T. Kawasaki, K. Ishikawa, H. Sekibata, I. Sato, K. Soai, Tetrahedron Lett. 2004, 45, 7939-7941;
69. m) T. Kawasaki, M. Shimizu, K. Suzuki, I. Sato, K. Soai, Tetrahedron: Asymmetry 2004, 15, 3699-3701.
70. For studies on the mechanism, see: a) I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama, K. Soai, Tetrahedron: Asymmetry 2003, 14, 975-979;
71. b) I. D. Gridnev, J. M. Serafimov, J. M. Brown, Angew. Chem. 2004, 116, 4992-4995;
72. Angew. Chem. Int. Ed. 2004, 43, 4884-4887;
73. c) D. G. Blackmond, Proc. Natl. Acad. Sci. USA 2004, 101, 5732-5736;
74. d) T. Buhse, Tetrahedron: Asymmetry 2003, 14, 1055-1061;
75. e) Y. Saito, H. Hyuga, J. Phys. Soc. Jpn. 2004, 73, 33-35;
76. f) G. Lente, J. Phys. Chem. A 2004, 108, 9475-9478.