Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

Tetrahedron Asymmetry

Volumn 23, Issue 14, 2012, Pages 1023-1027

  Shibata, Takanori ^a   Tarumi, Hikaru ^a   Kawasaki, Tsuneomi ^b   Soai, Kenso ^b  

^a WASEDA UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKANOL; DIISOPROPYL ZINC; PHENOL DERIVATIVE; PYRIMIDINE 5 CARBALDEHYDE; PYRIMIDYL ALKANOL; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALKYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REVIEW;

EID: 84865499251     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.07.010     Document Type: Article

References (43)

1. E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis II 1999 Springer-Verlag Berlin
2. E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis: Supplement 1 2003 Springer-Verlag Berlin
3. S.V. Malhotra, Methodologies in Asymmetric Catalysis 2004 American Chemical Society Washington, DC
4. I. Ojima, Catalytic Asymmetric Synthesis 3rd ed. 2010 Wiley-VCH New York
5. An excellent review of complete reversal of enantioselectivity using a single chiral source, see: T. Tanaka, and M. Hayahsi Synthesis 2008 3361 3376
6. T. Yamada, K. Imagawa, T. Nagata, and T. Mukaiyama Chem. Lett. 1992 2231 2234
7. G. Desimoni, G. Faita, A.G. Invernizzi, and P. Righetti Tetrahedron 53 1997 7671 7688
8. S. Kobayashi, and H. Ishitani J. Am. Chem. Soc. 116 1994 4083 4084
9. J. Balsells, and P.J. Walsh J. Am. Chem. Soc. 122 2000 1802 1803
10. A.M. Costa, C. Jimeno, J. Gavenonis, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 124 2002 6929 6941
11. M. Reetz, and G. Mehler Tetrahedron Lett. 44 2003 4593 4596
12. F. Lutz, T. Igarashi, T. Kawasaki, and K. Soai J. Am. Chem. Soc. 127 2005 12206 12207
13. F. Lutz, T. Igarashi, T. Kinoshita, M. Asahina, K. Tsukiyama, T. Kawasaki, and K. Soai J. Am. Chem. Soc. 130 2008 2956 2958
14. D. Lavabre, J.-C. Micheau, J.R. Islas, and T. Buhse J. Phys. Chem. A 111 2007 281 286
15. T. Kawasaki, Y. Wakushima, M. Asahina, K. Shiozawa, T. Kinoshita, F. Lutz, and K. Soai Chem. Commun. 47 2011 5277 5279
16. For a competitive asymmetric autocatalysis initiated by chiral β-amino alcohols: F. Lutz, I. Sato, and K. Soai Org. Lett. 6 2004 1613 1616
17. Recent reviews of asymmetric autocatalysis: (a) Soai, K.; Kawasaki, T.; Shibata, T. "Asymmetric Amplification and Autocatalysis" in the book of Ref. 1b, Chapter 12, pp 891-930.
18. K. Soai, and T. Kawasaki Asymmetric autocatalysis with amplification of chirality Topics Curr. Chem. 284 2008 1 33 (Amplification of Chirality)
19. T. Kawasaki, and K. Soai Bull. Chem. Soc. Jpn. 84 2011 879 892
20. T. Kawasaki, and K. Soai J. Fluorine Chem. 131 2010 525 534
21. L. Caglioti, B. Barabas, F. Faglioni, N. Florini, P. Lazzeretti, M. Maioli, K. Micskei, K. Rabai, F. Taddei, C. Zucchi, and G. Palyi Chimica Oggi 26 2008 30 31
22. G. Lente Symmetry 2 2010 767 798
23. T. Gehring, and D. Weingand Chirality 22 2010 E173 E182
24. Asymmetric autocatalysis with amplification of ee: K. Soai, T. Shibata, H. Morioka, and K. Choji Nature 378 1995 767 768
25. I. Sato, H. Urabe, S. Ishiguro, T. Shibata, and K. Soai Angew. Chem., Int. Ed. 42 2003 315 317
26. T. Shibata, S. Yonekubo, and K. Soai Angew. Chem., Int. Ed. 38 1999 659 661
27. Asymmetric autocatalysis in the presence of chiral initiators: K. Soai, S. Osanai, K. Kadowaki, S. Yonakubo, T. Shibata, and I. Sato J. Am. Chem. Soc. 121 1999 11235 11236
28. I. Sato, K. Kadowaki, and K. Soai Angew. Chem., Int. Ed. 39 2000 1510 1512
29. I. Sato, R. Yamashima, K. Kadowaki, J. Yamamoto, T. Shibata, and K. Soai Angew. Chem., Int. Ed. 40 2001 1096 1098
30. T. Kawasaki, M. Sato, S. Ishiguro, T. Saito, Y. Morishita, I. Sato, H. Nishino, Y. Inoue, and K. Soai J. Am. Chem. Soc. 127 2005 3274 3275
31. T. Kawasaki, K. Jo, H. Igarashi, I. Sato, M. Nagano, H. Koshima, and K. Soai Angew. Chem., Int. Ed. 44 2005 2774 2777
32. T. Kawasaki, H. Tanaka, T. Tsutsumi, T. Kasahara, I. Sato, and K. Soai J. Am. Chem. Soc. 128 2006 6032 6033
33. T. Kawasaki, K. Suzuki, Y. Hakoda, and K. Soai Angew. Chem., Int. Ed. 47 2008 496 499
34. Asymmetric autocatalysis triggered by chiral compounds arising from isotope substitution: I. Sato, D. Omiya, T. Saito, and K. Soai J. Am. Chem. Soc. 122 2000 11739 11740
35. T. Kawasaki, Y. Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, and K. Soai Science 324 2009 492 495
36. T. Kawasaki, Y. Okano, E. Suzuki, S. Takano, S. Oji, and K. Soai Angew. Chem., Int. Ed. 50 2011 8131 8133
37. Studies on the mechanisms of asymmetric autocatalysis: I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama, and K. Soai Tetrahedron: Asymmetry 14 2003 975 979
38. D.G. Blackmond, C.R. McMillan, S. Ramdeehul, A. Schorm, and J.M. Brown J. Am. Chem. Soc. 123 2001 10103 10104
39. I.D. Gridnev, J.M. Serafimov, and J.M. Brown Angew. Chem., Int. Ed. 43 2004 4884 4887
40. L. Schiaffino, and G. Ercolani Angew. Chem., Int. Ed. 47 2008 6832 6835
41. M. Quaranta, T. Gehring, B. Odell, J.M. Brown, and D.G. Blackmond J. Am. Chem. Soc. 132 2010 15104 15107
42. G. Ercolani, and L. Schiaffino J. Org. Chem. 76 2011 2619 2626
43. Asymmetric autocatalysis induced by chiral sec-alcohols: T. Shibata, K. Iwahashi, T. Kawasaki, and K. Soai Tetrahedron: Asymmetry 18 2007 1759 1762