Erratum to Amplification of Chirality and Enantioselectivity in the Asymmetric Autocatalytic Soai Reaction (ChemPhysChem, (2009), 10, (2508-2515), 10.1002/cphc.200900369);Amplification of chirality and enantioselectivity in the asymmetric autocatalytic Soai reaction

ChemPhysChem

Volumn 10, Issue 14, 2009, Pages 2508-2515

  Schiaffino, Luca ^a   Ercolani, Gianfranco ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

Asymmetric amplification; Asymmetric catalysis; Autocatalysis; Nucleophilic addition; Zinc

Indexed keywords

ADDITION REACTIONS; CHIRALITY; ENANTIOMERS; KINETICS; OLIGOMERS; ZINC;

AMPLIFICATION OF CHIRALITY; ASYMMETRIC AMPLIFICATION; ASYMMETRIC CATALYSIS; AUTOCATALYSIS; ENANTIOMERIC EXCESS; EXPERIMENTAL VALUES; LOW-TEMPERATURE REGIME; NUCLEOPHILIC ADDITIONS;

ENANTIOSELECTIVITY;

EID: 70349775663     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200900369     Document Type: Erratum

References (54)

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) A. Guijarro, M. Yus, The Origin of Chirality in the Molecules of Life, RSC, Cambridge, 2009.
4. a) K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768
5. b) K. Soai, T. Shibata, I. Sato, Acc. Chem. Res. 2000, 33, 382-390
6. c) K. Soai, T. Kawasaki, Chirality 2006, 18, 469-478
7. d) K. Soai, T. Kawasaki, Top. Curr. Chem. 2008, 284, 1-33.
8. a)T. Shibata, S. Yonekubo, K. Soai, Angew. Chem. 1999, 111, 746-748;
9. Angew. Chem. Int. Ed. 1999, 38, 659-661
10. b) I. Sato, H. Urabe, S. Ishiguro, T. Shibata, K. Soai, Angew. Chem. 2003, 115, 329-331;
11. Angew. Chem. Int. Ed. 2003, 42, 315-317.
12. a) Patent: K. Soai, T. Shibata, Y. Kowata, JP-Kokai 9-268179, 1997
13. b) 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
14. c) I. D. Gridnev, J. M. Serafimov, H. Quiney, J. M. Brown, Org. Biomol. Chem. 2003, 1, 3811-3819
15. d) B. Barabas, L. Caglioti, C. Zucchi, M. Maioli, E. Gál, K. Micskei, G. Pályi, J. Phys. Chem. B 2007, 111, 11506-11510.
16. D. A. Singleton, L. K. Vo, J. Am. Chem. Soc. 2002, 124, 10010-10011.
17. K. Mislow, Collect. Czech. Chem. Commun. 2003, 68, 849-864.
18. a) I. Sato, D. Omiya, K. Tsukiyama, Y. Ogi, K. Soai, Tetrahedron: Asymmetry 2001, 12, 1965-1969
19. b) I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama, K. Soai, Tetrahedron: Asymmetry 2003, 14, 975-979
20. c) T. Buhse, Tetrahedron: Asymmetry 2003, 14, 1055-1061
21. d) J. Rivera Islas, D. Lavabre, J.-M. Grevy, R. Hernandez Lamoneda, H. Rojas Cabrera, J.-C. Micheau, T Buhse, Proc. Natl. Acad. Sci. USA 2005, 102, 13743-13748
22. e) Y. Saito, H. Hyuga, J. Phys. Soc. Jpn. 2004, 73, 33-35
23. f) Y. Saito, H. Hyuga, J. Phys. Soc. Jpn. 2004, 73, 1685-1688.
24. a) D. G. Blackmond, C. R. McMillan, S. Ramdeehul, A. Schorm, J. M. Brown, J. Am. Chem. Soc. 2001, 123, 10103-10104
25. b) F. G. Buono, D. G. Blackmond, J. Am. Chem. Soc. 2003, 125, 8978-8979
26. c) D. G. Blackmond, Tetrahedron: Asymmetry 2006, 17, 584-589.
27. [8b,c] support the proposal of a tetrameric transition state, formed by two molecules of aldehyde and a diisopropylzinc-saturated dimer catalyst. Even if the transition state is tetrameric, the proposed mechanism complies with the dimer model because the latter term refers to the nature of the catalyst and not to that of the transition state.
28. I.D. Gridnev, J. M. Serafimov, J. M. Brown, Angew. Chem. 2004, 116, 4992-4995;
29. Angew. Chem. Int. Ed. 2004, 43, 4884-4887.
30. L. Schiaffino, G. Ercolani, Angew. Chem. 2008, 120, 6938-6941;
31. Angew. Chem. Int. Ed. 2008, 47, 6832-6835.
32. I. D. Gridnev, Chem. Lett. 2006, 35, 148-153.
33. a) J. Klankermayer, I.D. Gridnev, J. M. Brown, Chem. Commun. 2007, 3151-3153
34. b) J. M. Brown, I.D. Gridnev, J. Klankermayer, Top. Curr. Chem. 2008, 284, 35-65.
35. According to the mechanism of the Soai reaction recently proposed by us,1111 in compliance with the dimer model, two molecules of aldehyde and two molecules of diisopropylzinc are converted into a further dimer molecule per catalytic cycle.
36. See Supporting Information.
37. T Shibata, T. Hayase, J. Yamamoto, K. Soai, Tetrahedron: Asymmetry 1997,8, 1717-1719.
38. T Shibata, H. Morioka, T. Hayase, K. Choji, K. Soai, J. Am. Chem. Soc. 1996, 118, 471-472.
39. J. D. Hoffman, Numerical Methods for Engineers and Scientists, 2nd ed., Marcel Dekker, New York, 2001, p. 146.
40. F.G. Buono, H. Iwamura, D. G. Blackmond, Angew. Chem. 2004, 116, 2151 -2155;
41. Angew. Chem. Int. Ed. 2004, 43, 2099-2103.
42. The program, based on the Gauss-Newton algorithm, evaluates the first derivatives numerically and thus only required modification of the function evaluation subroutine. M. D. Johnston, Jr., Computational Chemistry, Elsevier, Amsterdam, 1988, pp. 498-507.
43. 3R).
44. I. D. Gridnev, J. M. Brown, Proc. Natl. Acad. Sci. USA 2004, 101, 5727-5731.
45. a) The functional M05-2X has been recently demonstrated to outperform the popular B3LYP functional in the energetic description of organic systems: M. D. Wodrich, C. Cormlnboeuf, P.R. Schreiner, A.A. Fokin, P. v. R. Schleyer, Org. Lett. 2007, 9, 1851-1854
46. b) Y. Zhao, D. G. Truhlar;, Acc. Chem. Res. 2008, 41, 157-167.
47. c. See: G. Ercolani, C. Piguet, M. Borkovec, J. Hamacek, J. Phys. Chem. B 2007, 111, 12195-12203, and references therein.
48. a) C. Girard, H.B. Kagan, Angew. Chem. 1998, 110, 3088-3127;
49. Angew. Chem. Int. Ed. 1998, 37, 2922-2959
50. b) T. Satyanarayana, S. Abraham, H. B. Kagan, Angew. Chem. 2009, 121, 464-503;
51. Angew. Chem. Int. Ed. 2009, 48, 456-494.
52. a) M. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832-4842
53. b) M. Kitamura, S. Suga, H. Oka, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800-9809.
54. We thank the anonymous reviewer for such a pedagogically useful remark.