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Volumn 72, Issue 26, 2007, Pages 10291-10293

Highly efficient synthesis of optically pure 5,5′,6,6′,7, 7′,8,8′-octahydro-1,1′-bi-2-naphthol and -naphthylamine derivatives by partial hydrogenation of 1,1′-binaphthyls with carbon nanofiber supported ruthenium nanoparticles

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHYLAMINE DERIVATIVES; PARTIAL HYDROGENATION; RUTHENIUM NANOPARTICLES;

EID: 37549060019     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702015j     Document Type: Article
Times cited : (22)

References (42)
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    • (b) Pu, L. Chem. Rev. 1998, 98, 2405.
    • (1998) Chem. Rev , vol.98 , pp. 2405
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    • 2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim, Germany, and references therein
    • (d) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000, and references therein.
    • (2000) Catalytic Asymmetric Synthesis
  • 5
    • 33947092416 scopus 로고    scopus 로고
    • 2,2′-Dimethoxy- and 2,2′-di(methoxymethy)oxy-1,1′- binaphthyl are well known as precursors for the 3,3′-disubstituted BINOL derivatives. (a) Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H. G.; Sogah, D. Y. J. Org. Chem. 1978, 43, 1930.
    • 2,2′-Dimethoxy- and 2,2′-di(methoxymethy)oxy-1,1′- binaphthyl are well known as precursors for the 3,3′-disubstituted BINOL derivatives. (a) Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H. G.; Sogah, D. Y. J. Org. Chem. 1978, 43, 1930.
  • 10
    • 0001940844 scopus 로고    scopus 로고
    • 6,6′-Disubstituted BINOL derivatives: (a) Mikami, K.; Motoyama, Y.; Terada, M. Inorg. Chim. Acta 1994, 222, 71.
    • 6,6′-Disubstituted BINOL derivatives: (a) Mikami, K.; Motoyama, Y.; Terada, M. Inorg. Chim. Acta 1994, 222, 71.
  • 20
    • 0030952111 scopus 로고    scopus 로고
    • 8-BINOL derivatives: (a) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080.
    • 8-BINOL derivatives: (a) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080.
  • 24
    • 0032540707 scopus 로고    scopus 로고
    • 8-DABN derivatives: (e) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808.
    • 8-DABN derivatives: (e) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808.
  • 25
    • 37549055385 scopus 로고    scopus 로고
    • 8-BINAP derivatives: (f) Zhang, X.; Matsumura, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Perkin Trans. 1 1994, 2309.
    • 8-BINAP derivatives: (f) Zhang, X.; Matsumura, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Perkin Trans. 1 1994, 2309.
  • 28
    • 0025930944 scopus 로고    scopus 로고
    • Representative papers: (a) Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
    • Representative papers: (a) Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
  • 32
    • 37549018041 scopus 로고    scopus 로고
    • Both BINOL and H8-BINOL lose their optical rotations by heating in alcohols over 100°C (∼2, and such partial racemization accelerates under acidic or basic conditions ∼56, Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A, Ed, John Wiley & Sons: New York, 1995; 1, p 397. Also see ref 2a
    • 8-BINOL lose their optical rotations by heating in alcohols over 100°C (∼2%), and such partial racemization accelerates under acidic or basic conditions (∼56%). Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, p 397. Also see ref 2a.
  • 33
    • 37549052095 scopus 로고    scopus 로고
    • The Pd/C-catalyzed reaction of (R)-BINOL can be performed at S/C, 100, but severe reaction conditions (100°C, 80 atm) are required to obtain H8-BINOL (99.7% ee) in high yields; see ref 7d
    • 8-BINOL (99.7% ee) in high yields; see ref 7d.
  • 34
    • 37549053988 scopus 로고    scopus 로고
    • Optically pure H8-BINAP is generally obtained by optical resolution of racemic H8-bis(diphenylphosphinyl)-1,1′- binaphthyl (H8-BINAPO, which is prepared from (±)-BINOL, followed by reduction with trichlorosilane; see ref 7a
    • 8-BINAPO), which is prepared from (±)-BINOL, followed by reduction with trichlorosilane; see ref 7a.
  • 36
    • 0027833694 scopus 로고    scopus 로고
    • The CNFs are classified into three types: graphite layers are perpendicular (platelet: CNF-P), parallel (tubular: CNF-T), and stacked obliquely (herringbone: CNF-H). These three CNFs can be synthesized selectively in large scales; see: (a) Rodriguez, N. M. J. Mater. Res. 1993, 8, 3233.
    • The CNFs are classified into three types: graphite layers are perpendicular (platelet: CNF-P), parallel (tubular: CNF-T), and stacked obliquely (herringbone: CNF-H). These three CNFs can be synthesized selectively in large scales; see: (a) Rodriguez, N. M. J. Mater. Res. 1993, 8, 3233.
  • 38
    • 37549061370 scopus 로고    scopus 로고
    • The solvent strongly affected the reaction rate; the hydrogenations of BINOL in THF and dichloroethane were both sluggish, and the H8-BINOL was obtained in <10% yields along with the formation of H4-BINOL in ca. 20 and 50% yields, respectively
    • 4-BINOL in ca. 20 and 50% yields, respectively.
  • 39
    • 37549020004 scopus 로고    scopus 로고
    • In the Pd/C-catalyzed reactions, similar results and explanations were reported; see ref 7d
    • In the Pd/C-catalyzed reactions, similar results and explanations were reported; see ref 7d.
  • 40
    • 37549055026 scopus 로고    scopus 로고
    • DABN 1f is easily soluble in THF, but the hydrogenation of 1f with Ru/CNF-P in THF at 100°C did not proceed.
    • DABN 1f is easily soluble in THF, but the hydrogenation of 1f with Ru/CNF-P in THF at 100°C did not proceed.
  • 41
    • 0021128488 scopus 로고    scopus 로고
    • Murdoch reported that chiral BINAP could be synthesized from optically pure DABN. Brown, K. J.; Berry, M. S.; Waterman, K. C.; Lingenfelter, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 4717.
    • Murdoch reported that chiral BINAP could be synthesized from optically pure DABN. Brown, K. J.; Berry, M. S.; Waterman, K. C.; Lingenfelter, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 4717.
  • 42
    • 37549060620 scopus 로고    scopus 로고
    • HPLC analysis was performed on an UV/vis detector (254 nm) using Daicel CHIRALCEL OD-H (flow rate = 0.5 mL/min).
    • HPLC analysis was performed on an UV/vis detector (254 nm) using Daicel CHIRALCEL OD-H (flow rate = 0.5 mL/min).


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