Asymmetric autocatalysis induced by cinnabar: Observation of the enantioselective adsorption of a 5-pyrimidyl alkanol on the crystal surface

Angewandte Chemie - International Edition

Volumn 52, Issue 35, 2013, Pages 9135-9138

  Shindo, Hitoshi ^a   Shirota, Yusuke ^a   Niki, Kaori ^a   Kawasaki, Tsuneomi ^b,c   Suzuki, Kenta ^b   Araki, Yuko ^b   Matsumoto, Arimasa ^b   Soai, Kenso ^b  

^a CHUO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c UNIVERSITY OF FUKUI   (Japan)

Author keywords

asymmetric amplification; atomic force microscopy; autocatalysis; cinnabar; homochirality

Indexed keywords

ADSORPTION STRUCTURES; ASYMMETRIC AMPLIFICATION; AUTOCATALYSIS; CINNABAR; ENANTIOSELECTIVE ADSORPTION; HOMOCHIRALITY; MICROCRYSTAL FORMATION; RELATED COMPOUNDS;

ATOMIC FORCE MICROSCOPY; ENANTIOSELECTIVITY;

ADSORPTION;

MERCURY DERIVATIVE; MERCURY SULFIDE; PYRIMIDINE DERIVATIVE;

ADSORPTION; ARTICLE; ASYMMETRIC AMPLIFICATION; ATOMIC FORCE MICROSCOPY; AUTOCATALYSIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HOMOCHIRALITY; PARTICLE SIZE; STEREOISOMERISM; SURFACE PROPERTY; X RAY CRYSTALLOGRAPHY;

ASYMMETRIC AMPLIFICATION; ATOMIC FORCE MICROSCOPY; AUTOCATALYSIS; CINNABAR; HOMOCHIRALITY;

ADSORPTION; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MERCURY COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PARTICLE SIZE; PYRIMIDINES; STEREOISOMERISM; SURFACE PROPERTIES;

EID: 84882937052     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304284     Document Type: Article

References (61)

1. M. Bolli, R. Micura, A. Eschenmoser, Chem. Biol. 1997, 4, 309-320
2. I. Weissbuch, M. Lahav, Chem. Rev. 2011, 111, 3236-3267
3. B. Kahr, R. W. Gurney, Chem. Rev. 2001, 101, 893-951
4. K. Mislow, Collect. Czech. Chem. Commun. 2003, 68, 849-864
5. B. L. Feringa, R. A. vanDelden, Angew. Chem. 1999, 111, 3624-3645
6. Angew. Chem. Int. Ed. 1999, 38, 3418-3438
7. 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
8. Angew. Chem. Int. Ed. 1999, 38, 3139-3154
9. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127
10. Angew. Chem. Int. Ed. 1998, 37, 2922-2959
11. D. K. Kondepudi, K. Asakura, Acc. Chem. Res. 2001, 34, 946-954
12. J. M. Ribo, J. Crusats, F. Sagues, J. Claret, R. Rubires, Science 2001, 292, 2063-2066
13. A. Guijarro, M. Yus, The Origin of Chirality in the Molecules of Life, Royal Society Chemistry, Cambridge, 2009
14. Y. Saito, H. Hyuga, Rev. Mod. Phys. 2013, 85, 603-621.
15. Chirality at the nanoscale, nanoparticles, surfaces, materials and more (Ed.:, D.B. Amabilino,), Wiley-VCH, Weinheim, 2009
16. K.-H. Ernst, Phys. Status Solidi B 2012, 249, 2057-2088
17. R. Raval, Chem. Soc. Rev. 2009, 38, 707-721
18. L. P. Garciaa, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941-967.
19. R. M. Hazen, in Progress in biological chirality (Eds.:, G. Palyi, C. Zucchi,), Elsevier, Oxford, 2004, Chap. 9, pp. 137-151
20. R. M. Hazen, D. S. Sholl, Nat. Mater. 2003, 2, 367-374
21. L. Vega, J. Breton, G. Girardet, L. Galatry, J. Chem. Phys. 1986, 84, 5171-5180.
22. B. Kahr, B. Chittenden, A. Rohl, Chirality 2006, 18, 127-133
23. W. A. Bonner, P. R. Kavasmaneck, F. S. Martin, J. J. Flores, Science 1974, 186, 143-144
24. R. M. Hazen, T. R. Filley, G. A. Goodfriend, Proc. Natl. Acad. Sci. USA 2001, 98, 5487-5490.
25. K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768
26. I. Sato, H. Urabe, S. Ishiguro, T. Shibata, K. Soai, Angew. Chem. 2003, 115, 329-331
27. Angew. Chem. Int. Ed. 2003, 42, 315-317
28. T. Shibata, T. Hayase, J. Yamamoto, K. Soai, Tetrahedron: Asymmetry 1997, 8, 1717-1719.
29. T. Kawasaki, I. Sato, H. Mineki, A. Matsumoto, K. Soai, J. Synth. Org. Chem. Jpn. 2013, 71, 109-123
30. T. Kawasaki, A. Matsumoto, K. Soai, Chim. Oggi 2012, 30, 10-13
31. T. Kawasaki, K. Soai, Bull. Chem. Soc. Jpn. 2011, 84, 879-892
32. K. Soai, T. Kawasaki, T. Shibata, Catalytic asymmetric synthesis, 3rded. (Ed.:, I. Ojima,), Wiley, Hoboken, New Jersey, 2010, pp. 891-930
33. K. Soai, T. Kawasaki, Chirality 2006, 18, 469-478
34. K. Soai, T. Kawasaki, Top. Curr. Chem. 2008, 284, 1-33.
35. J.-K. Micheau, C. Coudret, T. Buhse, The Soai Reaction and Related Topics (Eds.:, G. Palyi, C. Zucchi, L. Caglioti,), Accad. Nazl. Sci. Lett. Arti Modena, Modena, 2012, Chap. 7, pp. 169-196
36. T. Gehring, M. Busch, M. Schlageter, D. Weingand, Chirality 2010, 22, E 173 -E 182
37. B. Barabás, J. Toth, G. Pályi, J. Math. Chem. 2010, 48, 457-489
38. G. Lente, Symmetry 2010, 2, 767-798
39. J. M. Brown, I. Gridnev, J. Klankermayer, Top. Curr. Chem. 2008, 284, 35-65
40. L. Caglioti, G. Palyi, Chim. Oggi 2008, 26, 41-42.
41. I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama, K. Soai, Tetrahedron: Asymmetry 2003, 14, 975-979
42. M. Quaranta, T. Gehring, B. Odell, J. M. Brown, D. G. Blackmond, J. Am. Chem. Soc. 2010, 132, 15104-15107
43. G. Ercolani, L. Schiaffino, J. Org. Chem. 2011, 76, 2619-2626
44. J.-C. Micheau, C. Coudret, J.-M. Cruz, T. Buhse, Phys. Chem. Chem. Phys. 2012, 14, 13239-13248
45. T. Gehring, M. Quaranta, B. Odell, D. G. Blackmond, J. M. Brown, Angew. Chem. 2012, 124, 9677-9680
46. Angew. Chem. Int. Ed. 2012, 51, 9539-9542
47. I. D. Gridnev, A. K. Vorobiev, ACS Catal. 2012, 2, 2137-2149.
48. K. Soai, S. Osanai, K. Kadowaki, S. Yonekubo, T. Shibata, I. Sato, J. Am. Chem. Soc. 1999, 121, 11235-11236
49. I. Sato, K. Kadowaki, K. Soai, Angew. Chem. 2000, 112, 1570-1572
50. Angew. Chem. Int. Ed. 2000, 39, 1510-1512.
51. T. Kawasaki, Y. Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, K. Soai, Science 2009, 324, 492-495
52. T. Kawasaki, M. Sato, S. Ishiguro, T. Saito, Y. Morishita, I. Sato, H. Nishino, Y. Inoue, K. Soai, J. Am. Chem. Soc. 2005, 127, 3274-3275
53. K. Soai, I. Sato, T. Shibata, S. Komiya, M. Hayashi, Y. Matsueda, H. Imamura, T. Hayase, H. Morioka, H. Tabira, J. Yamamoto, Y. Kowata, Tetrahedron: Asymmetry 2003, 14, 185-188.
54. K. L. Aurivillius, Acta Chem. Scand. 1950, 4, 1413-1436.
55. B. Pal, S. Ikeda, B. Ohtani, Inorg. Chem. 2003, 42, 1518-1524.
56. A. Ben-Moshe, A. O. Govorov, G. Markovich, Angew. Chem. 2013, 125, 1313-1317
57. Angew. Chem. Int. Ed. 2013, 52, 1275-1279.
58. H. G. M. Edwards, Asian J. Phys. 1998, 7, 383-389.
59. D. J. Carter, A. L. Rohl, A. Shtukenberg, S. Bian, C. Hu, L. Baylon, B. Kahr, H. Mineki, K. Abe, T. Kawasaki, K. Soai, Cryst. Growth Des. 2012, 12, 2138-2145.
60. E. S. Dana, in The System of Mineralogy -Descriptive Mineralogy, 6thed., Wiley, New York, 1900, pp. 66-67.
61. CCDC938819 ((S)- 2) 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.