Synthesis of axially dissymmetric ligands with two chiral centers of perfluoroalkyl carbinol moiety, and their application to asymmetric synthesis

Current Organic Synthesis

Volumn 4, Issue 2, 2007, Pages 137-150

  Omote, Masaaki ^a   Sato, Kazuyuki ^a   Ando, Akira ^a   Kumadaki, Itsumaro ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

Axial dissymmetry; Carbinol; Chiral center; Fluorous; Ligand; Perfluoroalkyl; Recycling

Indexed keywords

EID: 34248656228     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017907780598880     Document Type: Review

References (59)

1. (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber., 1926, 59, 2159;
2. (b) Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc., 1979, 101, 3129-3131.
3. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev., 2003, 103(8), 3155-3211.
4. Pu, L. Chem. Rev., 1998, 98, 2405-2494.
5. Omote, M.; Ando, A.; Sato, K.; Kumadaki, I. Tetrahedron, 2001, 57, 8085-8094.
6. Chen, L.; Chen, G. J. J. Organomet. Chem., 1980, 193, 283-292.
7. (a) Omote, M.; Ando, A.; Takagi, T.; Koyama, M.; Kumadaki, I.; Shiro, M. Heterocycles, 1998, 47, 65-68;
8. (b) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett., 1990, 31, 611.
9. Activated Cu powder was prepared according to the following reference. Brewster, R. Q.; Groening, T. Org. Synthesis, Coll. Vol. II, 1948, 445-446.
10. Omote, M.; Kominato, A.; Sugawara, M.; Sato, K.; Ando, A.; Kumadaki, I. Tetrahedron Lett., 1999, 40, 5583-5585.
11. Omote, M.; Hasegawa, T.; Sato, K.; Ando, A.; Kumadaki, I. Heterocycles, 2003, 59(2), 501-504.
12. Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc., 1971, 93(22), 5908-5910.
13. Omote, M.; Nishimura, Y.; Sato, K.; Ando, A.; Kumadaki, I. Tetrahedron Lett., 2005, 46(2), 319-322.
14. Hasegawa, T.; Omote, M.; Sato, K.; Ando, A.; Kumadaki, I. Chem. Pharm. Bull., 2003, 51(3), 265-267.
15. Sokeirik, Y. S.; Sato, K; Omote, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem., 2006, 127(1), 150-152.
16. Nasipuri, D.; Bhattacharya, P. K. J. Chem. Soc., Perkin Trans. 1, 1977, 576-578.
17. Sokeirik, Y. S.; Sato, K.; Omote, M.; Ando, A.; Kumadaki, I. Tetrahedron Lett., 2006, 47(1), 2821-2824.
18. D for (S)-isomer is +23.2. Ramachandran, V.; Teodorvic, A.; Brown, H. C. Tetrahedron, 1993, 49, 1725-1738,
19. (a) Mori, M.; Nakai, T. Tetrahedron Lett., 1997, 38, (35) 6233-6236;
20. (b) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc., 2002, 124, (35), 10336-10348.
21. Ee was determined by GLC analysis using GAMMA DEX capillary column.
22. Omote, M.; Nishimura, Y.; Sato, K.; Ando, A.; Kumadaki, I. Tetrahedron, 2006, 62(8), 1886-1894.
23. Omote, M.; Nishimura, Y.; Sato, K.; Ando, A.; Kumadaki,I. J. Fluorine Chem., 2006, 127, 977-979.
24. (a) Zhu, D. W. Synthesis, 1993, 10, 953-954;
25. (b) Meinert, H.; Geister, U. J. Fluorine Chem., 1994, 68, 221-226;
26. (c) Chambers, R. D.; Sandford, G.; Shah, A. Synthetic Commun., 1996, 26, 1861-1866;
27. (d) Pozzi, G.; Montanari, F.; Rispens, M. T. Synthetic Commun., 1997, 27, 447-452;
28. (e) Sandford, G. Tetrahedron, 2003, 59, 437-454.
29. (a) Horváth, I. T.; Rábai, J. Science, 1994, 266, 72;
30. (b) Horváth, I.; Rábai, J. U.S. Patent, 5463082, 1995;
31. (c) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc., 1998, 120, 3133.
32. (a) Miura, T.; Inazu, T. Tetrahedron Lett., 2003, 44, 1819-1821;
33. (b) Chen, D.; Qing, F.; Huang, V. Org. Lett., 2002, 4, 1003-1005,
34. (c) Miura, T.; Hirose, Y.; Ohmae, M.; Inazu, T. Org. Lett., 2001, 3, 3947-3950;
35. (d) Wolf, E.; Richter, B.; Deelman, B.; Koten, G. J. Org. Chem., 2000, 65, 5422-5427;
36. (e) Richter, B.; Wolf, E.; Koten, G.; Deelman, B. J. Org. Chem., 2000, 65, 3885-3893.
37. (a) Matsugi, M.; Curran, D. P. Org. Lett., 2004, 6, 2717-2720;
38. (b) Curran, D. P.; Lou, Z. J. Am. Chem. Soc., 1999, 121, 9069-9072;
39. (c) Kainz, S.; Luo, Z.; Curran, D. P.; Leitner, W. Synthesis, 1998, 1425-1427;
40. (d) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem., 1887, 62, 6714-6715.
41. Nakamura, Y.; Takeuchi, S.; Zhang, S.; Okumura, K.; Ohgo, Y. Tetrahedron Lett., 2002, 43, 3053-3056.
42. (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron lett., 2000, 41, 57-60;
43. (b) Tian, Y.; Chan, K. S. Tetrahedron Lett., 2000, 41, 8813-8816;
44. (c) Tian, Y.; Chuan, Q.; Mak, C. W. T.; Chan, K. S. Tetrahedron, 2002, 58, 3951-3961;
45. (d) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron, 2002, 58, 3963-3969.
46. (a) Bayardon, J.; Sinou, D. J. Org. Chem., 2004, 69, 3121-3128;
47. (b) Bayardon, J.; Sinou, D. Tetrahedron Lett., 2003, 44, 1449-1451.
48. (a) Cavazzini, M.; Quich, S.; Pozzi, G. Tetrahedron Lett., 2002, 58, 3943-3949;
49. (b) Maillard, D.; Pozzi, G.; Quich, S.; Sinou, D. Tetrahedron Lett., 2002, 58, 3971-3976.
50. Shirakawa, S.; Tanaka, Y.; Maruoka, K. Org. Lett., 2004, 6, 1429-1431.
51. Omote, M.; Nishimura, Y.; Sato, K.; Ando, A.; Kumadaki, I. J. Fluorine Chem., 2005, 126(3), 407-409.
52. Bussehe-Hünnefeld, J. L.; Seebach, D. Tetrahedron, 1992, 48(27), 5719-5730.
53. Omote, M.; Tanaka, N.; Tarui, A.; Sato, K.; Kumadaki, I; Ando, A. Tetrahedron Lett., (submitted).
54. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc., 1981, 103, 2127-2129;
55. (b) Evans, D. A.; Taber, T. R. Tetrahedron Lett., 1980, 21, 4675-4678;
56. (c) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc., 1981, 103, 3099-3111.
57. Omote, M.; Nishimura, Y.; Sato, K.; Ando, A.; Kumadaki, I. J. Fluorine Chem., 2006, 127(1), 74-78.
58. Abiko, A.; Liu, J. F.; Buske, D. C.; Moriyama, S.; Masamune, S. J. Am. Chem. Soc., 1999, 121, 7168-7172.
59. Hayashi, T.; Matsumoto, Y.; Kiyoi, T.; Ito, Y.; Kohara, S.; Tomonaga, Y.; Hosomi, A. Tetrahedron Lett., 1988, 29, 5667-5670.