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)

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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.
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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.
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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.
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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.