Tandem (domino) and two-directional asymmetric catalysis of carbonyl-ene reaction with fluoral: Fluoral-ene approach to modeling of inter-smectic layer interaction of antiferroelectric liquid crystals

Synlett

Volumn , Issue 12, 1999, Pages 1895-1898

  Mikami, Koichi ^a   Yajima, Tomoko ^a   Siree, Nasakul ^a   Terada, Masahiro ^a   Suzuki, Yoshiichi ^b   Takanishi, Yoichi ^a   Takezoe, Hideo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Central Research and Development Laboratory   (Japan)

Author keywords

Antiferroelectric liquid crystals; Binaphthol titanium complex; Fluoral ene reaction; Vinyl sulfides; trifluoromethyl carbinols

Indexed keywords

CARBONYL DERIVATIVE; FLUORIDE SODIUM; METHANOL; TITANIUM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; LIQUID CRYSTAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032715187     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2990     Document Type: Article

References (61)

1. (a) Furukawa, K.; Terashima, K.; Ichihashi, M.; Saitoh, S.; Miyazawa, K.; Inukai, T. Ferroelectrics 1988, 85, 451.
2. (b) Chandani, A. D. L.; Hagiwara, T.; Suzuki, Y.; Ouchi, Y.; Takezoe, H.; Fukuda, A. Jpn. J. Appl. Phys. 1988, 27, L729.
3. (a) Suzuki, Y.; Nonaka, O.; Koide, Y.; Okabe, N.; Hagiwara, T.; Kawamura, I.; Yamamoto, N.; Yamada, Y.; Kitazume., T. Ferroelectrics 1993, 147, 109.
4. (b) Suzuki, Y.; Hagiwara, T.; Kawamura, I.; Okamura, N.; Kitazume, T.; Kakimoto, M.; Imai, Y.; Ouchi, Y.; Takezoe, H.; Fukuda, A. Liq. Cryst. 1989, 6, 167.
5. Takanishi, Y.; Hiraoka, K.; Agrawal, V. K.; Takezoe, H.; Fukuda, A.; Matsushita, M. Jpn. J. Appl. Phys. 1991, 30, 2023.
6. (a) Mikami, K.; Yajima, T.; Terada, M.; Kawauchi, S.; Suzuki, Y.; Kobayashi, I. Chem. Lett. 1996, 861. Mikami, K.; Siree, N.; Yajima, T.; Terada, M.; Suzuki, Y. 69th Annual Meeting of the Chemical Society of Japan, Tokyo, March 29th, 1995, Abstract No. 3H218.
7. (a) Mikami, K.; Yajima, T.; Terada, M.; Kawauchi, S.; Suzuki, Y.; Kobayashi, I. Chem. Lett. 1996, 861. Mikami, K.; Siree, N.; Yajima, T.; Terada, M.; Suzuki, Y. 69th Annual Meeting of the Chemical Society of Japan, Tokyo, March 29th, 1995, Abstract No. 3H218.
8. Also see. (b) Mikami, K.; Yajima, T.; Siree, N.; Terada, M.; Suzuki, Y.; Kobayashi, I. Synlett 1996, 837.
9. (c) Mikami, K.; Yajima, T.; Terada, M.; Suzuki, Y.; Kobayashi, I. Chem. Commun. 1997, 57.
10. A* on the basis of the polarized infrared spectroscopy. Jin, B.; Ling, Z.; Takanishi, Y.; Ishikawa, K.; Takezoe, H.; Fukuda, A.; Kakimoto, M.; Kitazume, T. Phys. Rev. 1996, E53, R4295.
11. Miyachi, K.; Matsushima, J.; Takanishi, Y.; Ishikawa, K.; Takezoe, H.; Fukuda, A. Phys. Rev. 1995, E52, R2153.
12. X-ray crystal analysis of bent conformations of AFLC molecules: (a) Hori, K.; Endo, K. Bull. Chem. Soc. Jpn. 1993, 66, 46.
13. (b) Hori, K.; Kawahara, S.; Ito, K. Ferroelectrics 1994, 147, 91.
14. (c) Ouchi, Y.; Yoshioka, Y.; Ishii, H.; Seki, K.; Kitamura, M.; Noyori, R.; Takanishi, Y.; Nishiyama, I. J. Mater. Chem. 1995, 5, 2297.
15. (d) Okuyama, K.; Kawano, N.; Uehori, S.; Noguchi, K.; Okabe, N.; Suzuki, Y.; Kawamura, I. Mol. Cryst. Liq. Cryst. 1996, 276, 193.
16. (a) Watanabe, J.; Hayashi, M. Macromolecules 1987, 20, 278. Watanabe, J.; Hayashi, M. Macromolecules 1989, 22, 4083. Nakata, Y.; Watanabe, J. J. Mater. Chem. 1994, 4, 1699.
17. (a) Watanabe, J.; Hayashi, M. Macromolecules 1987, 20, 278. Watanabe, J.; Hayashi, M. Macromolecules 1989, 22, 4083. Nakata, Y.; Watanabe, J. J. Mater. Chem. 1994, 4, 1699.
18. (a) Watanabe, J.; Hayashi, M. Macromolecules 1987, 20, 278. Watanabe, J.; Hayashi, M. Macromolecules 1989, 22, 4083. Nakata, Y.; Watanabe, J. J. Mater. Chem. 1994, 4, 1699.
19. (b) Suzuki, Y.; Isozaki, T.; Kusumoto, T.; Hiyama, T. Chem. Lett. 1995, 719. Kusumoto, T.; Isozaki, T.; Suzuki, Y.; Takanishi, Y.; Takezoe, H.; Fukuda, A.; Hiyama, T. Jpn. J. Appl. Phys. 1995, 34, L830. Suzuki, Y.; Isozaki, T.; Hashimoto, S.; Kusumoto, T.; Hiyama, T.; Takanishi, Y.; Takezoe, H. J. Mater. Chem. 1996, 6, 753.
20. (b) Suzuki, Y.; Isozaki, T.; Kusumoto, T.; Hiyama, T. Chem. Lett. 1995, 719. Kusumoto, T.; Isozaki, T.; Suzuki, Y.; Takanishi, Y.; Takezoe, H.; Fukuda, A.; Hiyama, T. Jpn. J. Appl. Phys. 1995, 34, L830. Suzuki, Y.; Isozaki, T.; Hashimoto, S.; Kusumoto, T.; Hiyama, T.; Takanishi, Y.; Takezoe, H. J. Mater. Chem. 1996, 6, 753.
21. (b) Suzuki, Y.; Isozaki, T.; Kusumoto, T.; Hiyama, T. Chem. Lett. 1995, 719. Kusumoto, T.; Isozaki, T.; Suzuki, Y.; Takanishi, Y.; Takezoe, H.; Fukuda, A.; Hiyama, T. Jpn. J. Appl. Phys. 1995, 34, L830. Suzuki, Y.; Isozaki, T.; Hashimoto, S.; Kusumoto, T.; Hiyama, T.; Takanishi, Y.; Takezoe, H. J. Mater. Chem. 1996, 6, 753.
22. Reviews on tandem reaction sequences as the combination of multiple reactions in single operation to maximize synthetic efficiency: (a) Posner, G. Chem. Rev. 1986, 86, 831.
23. (b) Ziegler, F. Chem. Rev. 1988, 88, 1423.
24. (c) Mikami, K.; Nakai, T. Synthesis 1991, 594. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. Nakai, T.; Mikami, K. Kagaku no Ryoiki 1982, 36, 661 [ Chem. Abstr. 1982, 96, 16001].
25. (c) Mikami, K.; Nakai, T. Synthesis 1991, 594. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. Nakai, T.; Mikami, K. Kagaku no Ryoiki 1982, 36, 661 [ Chem. Abstr. 1982, 96, 16001].
26. (c) Mikami, K.; Nakai, T. Synthesis 1991, 594. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. Nakai, T.; Mikami, K. Kagaku no Ryoiki 1982, 36, 661 [ Chem. Abstr. 1982, 96, 16001].
27. (c) Mikami, K.; Nakai, T. Synthesis 1991, 594. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. Nakai, T.; Mikami, K. Kagaku no Ryoiki 1982, 36, 661 [ Chem. Abstr. 1982, 96, 16001].
28. (d) Waldmann, H.; Nachr. Chem. Techn. Lab. 1992, 40, 828.
29. (e) Ho, T.-L. Tandem Organic Reactions, Wiley: New York, 1992.
30. (f) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed Engl. 1993, 32, 131.
31. (g) Denmark, S. E.; Thorarensen. A. Chem. Rev. 1996, 96, 137.
32. Reviews on two-directional chain synthesis: (a) Schreiber, S. L. Chemica Scripta 1987, 27, 563.
33. (b) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
34. (c) Magnuson, S. R. Tetrahedron 1995, 51, 2167.
35. Reviews on ene reactions: (a) Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis; Jacobsen, H. E.; Pfaltz, A.; Yamamoto H., Eds.; Springer: Heidelberg, in press. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1990, 48, 292.
36. Reviews on ene reactions: (a) Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis; Jacobsen, H. E.; Pfaltz, A.; Yamamoto H., Eds.; Springer: Heidelberg, in press. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1990, 48, 292.
37. Reviews on ene reactions: (a) Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis; Jacobsen, H. E.; Pfaltz, A.; Yamamoto H., Eds.; Springer: Heidelberg, in press. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1990, 48, 292.
38. (b) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991; Vols. 2 and 5.
39. (c) Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476.
40. (d) Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1969, 8, 556.
41. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
42. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
43. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
44. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
45. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
46. Reviews on asymmetric catalysis by chiral titanium complexes: Mikami, K.; Terada, M. In Lewis Acid Reagents: A Practical Approach; Yamamoto H., Ed.; Oxford University Press: Oxford, 1998; p 93. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1991, 49, 566. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods Vol. 3; Scheffold, R., Ed.; Springer: Berlin, 1983, p 217.
47. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282.
48. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282.
49. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282.
50. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282.
51. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1992, 71, 14. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282.
52. For a tandem and two-directional prototropic ene-type aldol reaction, see: Mikami, K.; Matsukawa, S.; Nagashima, M.; Funabashi, H.; Morishima, H. Tetrahedron Lett. 1997, 38, 579.
53. Mikami, K.; Yajima, T.; Terada, M.; Uchimaru, T. Tetrahedron Lett. 1993, 34, 7591. Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087. Mikami, K.; Yajima, T.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta, M. Tetrahedron 1996, 52, 85.
54. Mikami, K.; Yajima, T.; Terada, M.; Uchimaru, T. Tetrahedron Lett. 1993, 34, 7591. Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087. Mikami, K.; Yajima, T.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta, M. Tetrahedron 1996, 52, 85.
55. Mikami, K.; Yajima, T.; Terada, M.; Uchimaru, T. Tetrahedron Lett. 1993, 34, 7591. Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087. Mikami, K.; Yajima, T.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta, M. Tetrahedron 1996, 52, 85.
56. For vinylic sulfides as reactive ene components: Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Terada, M.; Matsukawa, S.; Mikami, K. J. Chem. Soc., Chem. Commun. 1993, 327.
57. For vinylic sulfides as reactive ene components: Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Terada, M.; Matsukawa, S.; Mikami, K. J. Chem. Soc., Chem. Commun. 1993, 327.
58. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
59. 13C NMR analysis through comparison with the E-isomer. The C3 of the Z-isomer absorbs downfield than that of the E-diastereomer (Scheme 3).
60. 1H NMR spectroscopy after the column chromatography.
61. R (190 °C) anti,E-4 19.1 min, syn,E-4 18.6 min, anti,Z-4 17.4 min, synZ-4 18.0 min.