Quantification of sophisticated equilibria in the reaction pool and amplifying catalytic cycle of the soai reaction

ACS Catalysis

Volumn 2, Issue 10, 2012, Pages 2137-2149

  Gridnev, Ilya D ^a,c   Vorobiev, Andrey Kh ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

Autocatalysis; DFT computations; Soai reaction; Solvent effects; Zn alcoholates

Indexed keywords

ALCOHOLATE; AUTOCATALYSIS; CATALYTIC CYCLES; CHIRAL AMPLIFICATION; CONFORMATIONAL ANALYSIS; DENSITY FUNCTIONAL THEORIES (DFT); DFT COMPUTATIONS; ENANTIOSELECTIVE ALKYLATION; HOMOCHIRAL; MACROCYCLICS; RELATIVE ABUNDANCE; SOAI REACTION; SOLVENT EFFECTS; TETRAMER FORMS; TETRAMERS; THERMODYNAMIC PARAMETER;

ALDEHYDES; DENSITY FUNCTIONAL THEORY; DIMERS; LAKES; ZINC;

CONFORMATIONS;

EID: 84868577214     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300497h     Document Type: Article

References (63)

1. Soai, K.; Shibata, T.; Morioka, H.; Shoji, K. Nature 1995, 378, 767.
2. Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382.
3. Soai, K.; Kawasaki, T. Chirality 2006, 18, 469.
4. Soai, K.; Kawasaki, T. Top. Curr. Chem. 2008, 271-274, 1.
5. Kawasaki, T.; Soai, K. Bull. Chem. Soc. Jpn. 2011, 84, 879.
6. Soai, K.; Shibata, T.; Kowata, Y. JP-Kokai 9-268179, 1997.
7. Singleton, D. A.; Vo, L. K. J. Am. Chem. Soc. 2002, 124, 10010.
8. Soai, K.; Sato, I.; Shibata, T.; Komiya, S.; Hayashi, M.; Matsueda, Y.; Imamura, H.; Hayase, T.; Morioka, H.; Tabira, H.; Yamamoto, J.; Kowata, Y. Tetrahedron: Asymmetry 2003, 14, 185.
9. Gridnev, I. D.; Serafimov, J. M.; Quiney, H.; Brown, J. M. Org. Biomol. Chem. 2003, 1, 3811.
10. Singleton, D. A.; Vo, L. K. Org. Lett. 2003, 5, 4337.
11. Kawasaki, T.; Suzuki, K.; Shimizu, M.; Ishikawa, K.; Soai, K. Chirality 2006, 18, 479.
12. Barabas, B.; Caglioti, L.; Zucchi, C.; Maioli, M.; Gal, E.; Micskei, K.; Palyi, G. J. Phys. Chem. B 2007, 111, 11506.
13. Micskei, K.; Rabai, G.; Gal, E.; Caglioti, L.; Palyi, G. J. Phys. Chem. B 2008, 112, 9196.
14. Suzuki, K.; Hatase, K.; Nishiyama, D.; Kawasaki, T.; Soai, K. J. Syst. Chem. 2010, 1, 5.
15. Frank, F. C. Biochim. Biophys. Acta 1953, 11, 459.
16. Avetisov, V.; Goldanskii, V. I. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 11435.
17. Goldanskii, V. I.; Kuzmin, V. V. Z. Phys. Chem. (Leipzig) 1988, 269, 216.
18. Mislow, K. Collect. Czech. Chem. Commun. 2003, 68, 849-864.
19. Caglioti, L.; Hajdu, C.; Holczknecht, O.; Zékány, L.; Zucchi, C.; Micskei, K.; Pályi, G. Viva Origino 2006, 34, 62.
20. Buhse, T. Tetrahedron: Asymmetry 2003, 14, 1055.
21. Islas, J. R.; Lavabre, D.; Grevy, J.-M.; Lamoneda, R. H.; Cabrera, H. R.; Micheau, J.-C.; Buhse, T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 13743.
22. Blackmond, D. G. Tetrahedron: Asymmetry 2006, 17, 584.
23. Islas, J. R.; Buhse, T. J. Mex. Chem. Soc. 2007, 51, 117.
24. Ribo, J. M.; Hochberg, D. Phys. Lett. A 2008, 373, 111-122.
25. Crusats, J.; Hochberg, D.; Moyano, A.; Ribo, J. M. Chem. Phys. Chem 2009, 10, 2123-2131.
26. Micheau, J.-C.; Cruz, J.-M.; Coudret, C.; Buhse, T. Chem. Phys. Chem 2010, 11, 3417-3419.
27. Blackmond, D. G. Tetrahedron: Asymmetry 2010, 21, 1630-1634.
28. Doka, E.; Lente, G. J. Am. Chem. Soc. 2011, 133, 17878-17881.
29. Gridnev, I. D. Chem. Lett. 2006, 148-153.
30. Gehring, T.; Busch, M.; Schlageter, M.; Weingand, D. Chirality 2010, 22, 173-182.
31. Gridnev, I. D.; Serafimov, J. M.; Brown, J. M. Angew. Chem., Int. Ed. 2004, 43, 4884-4487.
32. Klankermayer, J.; Gridnev, I. D.; Brown, J. M. Chem. Commun. 2007, 3151-3153.
33. Brown, J. M.; Gridnev, I. D.; Klankermayer, J. Top. Curr. Chem. 2008, 284, 35-65.
34. Quaranta, M.; Gehring, T.; Odell, B.; Brown, J. M.; Blackmond, D. G. J. Am. Chem. Soc. 2010, 132, 15104-15107.
35. Blackmond, D. G.; McMillan, C. R.; Ramdeehul, S.; Schorm, A.; Brown, J. M. J. Am. Chem. Soc. 2001, 123, 10103-10105.
36. Buono, F. G.; Blackmond, D. G. J. Am. Chem. Soc. 2003, 125, 8978-8979.
37. Buono, F. G.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 2099-2103.
38. Gridnev, I. D.; Brown, J. M. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5727-5731.
39. Schiaffino, L.; Ercolani, G. Angew. Chem., Int. Ed. 2008, 47, 6832- 6835.
40. Schiaffino, L.; Ercolani, G. ChemPhysChem. 2009, 10, 2508-2515.
41. Schiaffino, L.; Ercolani, G. Chem.-Eur. J. 2010, 16, 3147-3156.
42. Ercolani, G.; Schiaffino, L. J. Org. Chem. 2011, 76, 2619-2626.
43. Gridnev, I. D.; A. K. Vorob'ev, Raskatov, E. A. Role of Oligomerization in Soai Reaction: Structures, Energies, Possible Reactivity. In The Soai Reaction and Related Topic; G. Pályi, Zucchi, C., Caglioti, L., Eds.; Artestampa: Modena, Italy, 2012; pp 79-122.
44. Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 59-661.
45. Busch, M.; Schlageter, M.; Weingand, D.; Gehring, T. Chem.- Eur. J. 2009, 15, 8251-8258.
46. By line shape analysis of the signals of pyrimidinyl protons from homo- and heterochiral 2 as it was described in ref 31 for another catalyst. Reich., H. J. WINDNMR, Line shape analysis software; 2005.
47. Dennis, J. E.; Gay, D. M.; Welsch, R. E. IEEE/ACM Trans. Math. Software 1981, 7, 348-383.
48. Chang, C. E.; Chen, W.; Gilson, M. K. J. Chem. Theory Comput. 2005, 1, 1017.
49. Carlsson, J.; Aqvist, J. J. Phys. Chem. B 2005, 109, 6448.
50. Singh, N.; Warshel, A. J. Phys. Chem. B 2009, 113, 7372.
51. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
52. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
53. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
54. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
56. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
57. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
58. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
59. Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209.
60. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
61. Peng, C. Y.; Schlegel, B. Isr. J. Chem. 1994, 34, 449.
62. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
63. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.