Mechanistic insights in the reversal of enantioselectivity of chiral catalysts by achiral catalysts in asymmetric autocatalysis

Journal of the American Chemical Society

Volumn 130, Issue 10, 2008, Pages 2956-2958

  Lutz, François ^a   Igarashi, Takashi ^a   Kinoshita, Tomoyuki ^a   Asahina, Mai ^a   Tsukiyama, Koichi ^a   Kawasaki, Tsuneomi ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; KINETICS;

ALCOHOLS; ALDEHYDES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHENYLPROPANOLAMINE; STEREOISOMERISM; ZINC;

EID: 41549113413     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077156k     Document Type: Article

References (53)

1. (a) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 7678.
2. (b) Soai, K.; Osanai, S.; Kadowaki, K.; Yonekubo, S.; Shibata, T.; Sato, I. J. Am. Chem. Soc. 1999, 121, 11235-11236.
3. (c) Kawasaki, T.; Sato, M.; Ishiguro, S.; Saito, T.; Morishita, Y.; Sato, I.; Nishino, H.; Inoue, Y.; Soai, K. J. Am. Chem. Soc. 2005, 127, 3274-3275.
4. (d) Kawasaki, T.; Tanaka, H.; Tsutsumi, T.; Kasahara, T.; Sato, I.; Soai, K. J. Am. Chem. Soc. 2006, 128, 6032-6033.
5. Reviews: (e) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659.
6. (f) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390.
7. (g) Soai, K.; Sato, I.; Shibata, T. Chem. Record 2001, 1, 321-332.
8. (h) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222.
9. (i) Milsow, K. Coll. Czech. Chem. Commun. 2003, 68, 849-864.
10. (j) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073.
11. (k) Blackmond, D. G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5732-5736.
12. (l) Podlech, J.; Gehring, T. Angew. Chem., Int. Ed. 2005, 44, 5776-5777.
13. (m) Micskei, K.; Maioli, M.; Zucchi, C.; Caglioti, L.; Palyi, G. Tetrahedron: Asymmetry 2006, 17, 2960-2962.
14. (a) Lutz, F.; Igarashi, T.; Kawasaki, T.; Soai, K. J. Am. Chem. Soc. 2005, 127, 12206-12207.
15. (b) Lavabre, D.; Micheau, J.-C.; Islas, J. R.; Buhse, T. J. Phys. Chem. A 2007, 111, 281-286.
16. (a) Sato, I.; Omiya, D.; Tsukiyama, K.; Ogi, Y.; Soai, K. Tetrahedron: Asymmetry 2001, 12, 1965-1969.
17. Also see the Supporting Information for a kinetic study of the reaction until completion. For other kinetic studies of asymmetric autocatalysis, see: (b) Blackmond, D. G.; McMillan, C. R.; Ramdeehul, S.; Shorm, A.; Brown, J. M. J. Am. Chem. Soc. 2001, 123, 10103-10104.
18. (c) Sato, I.; Omiya, D.; Igarashi, H.; Kato, K.; Ogi, Y.; Tsukiyama, K.; Soai, K. Tetrahedron: Asymmetry 2003, 14, 975-979.
19. (d) Buono, F. G.; Blackmond, D. G. J. Am. Chem. Soc. 2003, 125, 8978-8979.
20. (e) Saito, Y.; Hyuga, H. J. Chem. Soc. Jpn. 2004, 73, 33-35.
21. (f) Lente, G. J. Phys. Chem. A 2004, 108, 9475-9478 .
22. (g) 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, 13743-13748.
23. Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800-9809.
24. In the mutual inhibibition model explicited in ref 2b, a reversal of enantioselectivity may not occur before asymmetric autocatalysis starts.
25. (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
26. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
27. (c) Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. J. Chem. Soc., Chem. Commun. 1993, 182-183.
28. (d) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
29. (e) Rijnberg, E.; Hovestad, N. J.; Kleij, A. W.; Jastrzebski, J. T. B. H.; Boersma, J.; Janssen, M. D.; Spek, A. L.; van Koten, G. Organometallics 1997, 16, 2847-2857.
30. (f) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem.-Eur. J. 2002, 8, 5211-5218.
31. (a) Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605-3614.
32. (b) Asakura, K.; Yamamoto, T.; Inoue, S.; Osanai, S.; Kondepudi, D. K.; Yamaguchi, T. Chem. Phys. Lett. 2005, 406, 312-317.
33. (c) Rasmussen, T.; Norrby, P. O. J. Am. Chem. Soc. 2001, 123, 2464-2465.
34. Puchot, C.; Samuel. O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357.
35. 2/ab. Representative simulations are shown in the Supporting Information.
36. c). Representative simulations are shown in the Supporting Information.
37. For the kinetic aspects of nonlinear effects, see: (a) Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12935.
38. (b) Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402-411.
39. 1H NMR spectra of the isopropylzinc alkoxides issued from DMNE, DBAE, and their mixture in deuterated toluene were too complex to be fully interpreted, NMR spectroscopy showed that the isopropylzinc alkoxide issued from the mixture of DMNE and DBAE forms preferentially another complex(es) than when they are alone. Charts and their comments are shown in the Supporting Information.
40. (a) Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem.-Eur. J. 1996, 2, 1173-1181.
41. (b) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
42. For possible structures of zinc alkoxides of pyrimidyl alkanol. see: (c) Gridnev, I. D.; Serafimov, J. M.; Brown, J. M. Angew. Chem., Int. Ed. 2004, 43, 4884-4887.
43. (d) Klankermayer, J.; Gridnev, I. D.; Brown, J. M. Chem. Commun. 2007, 3151-3153.
44. For the use of achiral additives as a mean to improve the activity or the enantioselectivity of chiral catalysts, see: (a) Soai, K.; Hayasaka, T.; Ugajin, S. Chem. Commun. 1989, 516-517.
45. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636-3638.
46. (c) Wieland, L. C.; Deng, H.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 15453-15456.
47. Reviews: (d) Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem.. Int. Ed. 1999, 38, 1570-1577.
48. (e) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
49. (f) Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297-3344.
50. For scarce examples of reversal of enantioselectivity using achiral additives bearing different functional groups than the mononuclear chiral catalyst, see: (a) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett. 1992, 2231-2234.
51. (b) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. Tetrahedron 1997, 53, 7671-7688.
52. (c) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929-6941.
53. (d) Reetz, M.; Mehler, G. Tetrahedron Lett. 2003, 44, 4593-4596.