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Volumn 3, Issue 5, 2007, Pages 243-249

Stereochemistry in Lewis acid-catalyzed silylation of alcohols, silanols, and methoxysilanes with optically active methyl(1-naphthyl)phenylsilane

Author keywords

Chiral silicon center; Enantiomeric excess (ee); Optical purity; Optically active; Silylation reaction; Stereochemistry; Tris(pentafluorophenyl)borane

Indexed keywords


EID: 33947623192     PISSN: 15690660     EISSN: 15728994     Source Type: Journal    
DOI: 10.1007/s11201-007-9026-y     Document Type: Article
Times cited : (38)

References (16)
  • 1
    • 0010290459 scopus 로고
    • A Facile Synthesis of Disiloxanes with Functional Groups
    • (a) (b) Mori, A., Sato, H., Mizuno, K., Hiyama, T., Shintani, K. & Kawakami, Y. 1996 A Facile Preparation and Polymerization of 1,1-Difunctionalized Disiloxanes, Chem. Lett. 517-518; (c) Kawakami, Y., Aoki, T., Hisada, H., Yamamura, Y. & Yamashita, Y. 1985 Poly(p -disiloxane substituted styrene)s as materials for oxygen permeable membranes, Polym. Commun. 26, 133-136; (d) Kawakami, Y., Karasawa, H., Kamiya, H. & Yamashita, Y. 1986 The role of p -oligosiloxane substituents of polystyrene in selective oxygen permeation through the polymer film, Polym. J. 18, 237-241; (e) Kawakami, Y., Kishimoto, N., Takeshita, K. & Watanabe, T. 1999 Relaxation study of poly[(4-oligodimethylsiloxanyl)styrene]s by solid state 29 Si NMR', Design Monom. Polym. 2, 93-101; (f) Cho, Y. H., He, M., Kim, B. K. & Kawakami, Y. 2004 Improvement of holographic performance by Novel photopolymer systems with siloxane-containing epoxides, Sci. Tech. Adv. Mater. 5, 319-323; (g) He, M., Cho, Y.H., Kim
    • (a) Mori, A., Hishida, T., Soga, Y. & Kawakami, Y. 1995 A Facile Synthesis of Disiloxanes with Functional Groups, Chem. Lett. 107-108; (b) Mori, A., Sato, H., Mizuno, K., Hiyama, T., Shintani, K. & Kawakami, Y. 1996 A Facile Preparation and Polymerization of 1,1-Difunctionalized Disiloxanes, Chem. Lett. 517-518; (c) Kawakami, Y., Aoki, T., Hisada, H., Yamamura, Y. & Yamashita, Y. 1985 Poly(p -disiloxane substituted styrene)s as materials for oxygen permeable membranes, Polym. Commun. 26, 133-136; (d) Kawakami, Y., Karasawa, H., Kamiya, H. & Yamashita, Y. 1986 The role of p -oligosiloxane substituents of polystyrene in selective oxygen permeation through the polymer film, Polym. J. 18, 237-241; (e) Kawakami, Y., Kishimoto, N., Takeshita, K. & Watanabe, T. 1999 Relaxation study of poly[(4-oligodimethylsiloxanyl)styrene]s by solid state 29 Si NMR', Design Monom. Polym. 2, 93-101; (f) Cho, Y. H., He, M., Kim, B. K. & Kawakami, Y. 2004 Improvement of holographic performance by Novel photopolymer systems with siloxane-containing epoxides, Sci. Tech. Adv. Mater. 5, 319-323; (g) He, M., Cho, Y.H., Kim, N. & Kawakami, Y. 2005 Transmission holographic gratings using (siloxane and mesogen)-containing compounds, Design. Monom. Polym. 8, 473-486; (h) Cho, Y.H., Kawade, R., Kubota, T. & Kawakami, Y. 2005 Control of morphology and diffraction efficiency of holographic gratings using siloxane-containing reactive diluent, Sci. Tech. Adv. Mater. 6, 435-442; (i) Cho, Y.H., Shin, W., Kim, N., Kim, B.K. & Kawakami, Y. 2005 High-performance transmission holographic gratings via different polymerization rates of dipentaerythritol acrylates and siloxane-containing epoxides, Chem. Mater. 17, 6263-6271; (j) Kawakami, Y., Cho, Y.H., He, M. & Xue, L. 2006 Design of polysiloxane materials for electronic applications, Mol. Cryt. Liq. Cryst. 447, 189-202.
    • (1995) Chem. Lett. , pp. 107-108
    • Mori, A.1    Hishida, T.2    Soga, Y.3    Kawakami, Y.4
  • 2
    • 0032634786 scopus 로고    scopus 로고
    • Catalytic cross-dehydrocoupling polymerization of 1,4-bis(dimethylsilyl)benzene with water. A new approach to poly(oxydimethylsilyl)benzene
    • Li, Y. & Kawakami, Y. 1999 Catalytic cross-dehydrocoupling polymerization of 1,4-bis(dimethylsilyl)benzene with water. A new approach to poly(oxydimethylsilyl)benzene, Macromolecules 32, 3540-3542.
    • (1999) Macromolecules , vol.32 , pp. 3540-3542
    • Li, Y.1    Kawakami, Y.2
  • 3
    • 0032595878 scopus 로고    scopus 로고
    • 3 catalyzed cross-dehydrocoupling polymerization of bis(hydrosilane)s with diols
    • (a) (b) Li, Y. & Kawakami, Y. 1999 Synthesis and properties of polymers containing silphenylene moiety via catalytic cross-dehydrocoupling polymerization of 1,4-Bis(dimethylsilyl)benzene, Macromolecules 32, 8768-8773
    • 3 catalyzed cross-dehydrocoupling polymerization of bis(hydrosilane)s with diols, Macromolecules 32, 6871-6873; (b) Li, Y. & Kawakami, Y. 1999 Synthesis and properties of polymers containing silphenylene moiety via catalytic cross-dehydrocoupling polymerization of 1,4-Bis(dimethylsilyl)benzene, Macromolecules 32, 8768-8773.
    • (1999) Macromolecules , vol.32 , pp. 6871-6873
    • Li, Y.1    Kawakami, Y.2
  • 4
    • 0031124464 scopus 로고    scopus 로고
    • Synthesis of poly(tetramethyl-m-silphenylenesiloxane), an elastomer of enhanced high-temperature stability
    • (a) (b) Zhang, R., Mark, J.E. & Pinhas, A.R. 2000 Dehydrocoupling polymerization of bis-silanes and disilanols to poly(silphenylenesiloxane) as catalyzed by rhodium complexes, Macromolecules 33, 3508-3510; (c) Homrighausen, C.L. & Keller, T.M. 2002 Synthesis of hydroxy-terminated, oligomeric poly(silarylene disiloxane)s via rhodium-catalyzed dehydrogenative coupling and their use in the aminosilane-disilanol polymerization reaction, J. Polym. Sci.: Part A: Polym. Chem. 40, 1334-1341
    • (a) Zhang, R., Pinhas, A.R. & Mark, J.E. 1997 Synthesis of poly(tetramethyl- m -silphenylenesiloxane), an elastomer of enhanced high-temperature stability, Macromolecules 30, 2513-2515; (b) Zhang, R., Mark, J.E. & Pinhas, A.R. 2000 Dehydrocoupling polymerization of bis-silanes and disilanols to poly(silphenylenesiloxane) as catalyzed by rhodium complexes, Macromolecules 33, 3508-3510; (c) Homrighausen, C.L. & Keller, T.M. 2002 Synthesis of hydroxy-terminated, oligomeric poly(silarylene disiloxane)s via rhodium-catalyzed dehydrogenative coupling and their use in the aminosilane-disilanol polymerization reaction, J. Polym. Sci.: Part A: Polym. Chem. 40, 1334-1341.
    • (1997) Macromolecules , vol.30 , pp. 2513-2515
    • Zhang, R.1    Pinhas, A.R.2    Mark, J.E.3
  • 5
    • 0000935398 scopus 로고
    • (a) (b) Babu, G.N. & Newmark, R.A. 1991 Polymerization of 1,4-bis(hydroxydimethylsilyl)benzene with (dimethylamino)/chlorosilanes: Structural characterization by silicon-29 NMR, Macromolecules 24, 4503-4509
    • (a) Pike, R.M. 1961 J. Polym. Sci. 50, 151; (b) Babu, G.N. & Newmark, R.A. 1991 Polymerization of 1,4-bis(hydroxydimethylsilyl)benzene with (dimethylamino)/chlorosilanes: Structural characterization by silicon-29 NMR, Macromolecules 24, 4503-4509.
    • (1961) J. Polym. Sci. , vol.50 , pp. 151
    • Pike, R.M.1
  • 6
    • 0000323495 scopus 로고
    • The piperidine-catalyzed reaction of triphenylsilane with some hydroxy compounds
    • Gilman, H., Dunn, G.E., Hartzfeld, H. & Smith, A.G. 1955 The piperidine-catalyzed reaction of triphenylsilane with some hydroxy compounds, J. Am. Chem. Soc. 77, 1287-1288.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 1287-1288
    • Gilman, H.1    Dunn, G.E.2    Hartzfeld, H.3    Smith, A.G.4
  • 7
    • 0004049506 scopus 로고
    • Silane-silanol dehydrocondensation. The microscopic reverse of hydrogen activation by an organometallic oxide complex
    • Klingler, R. J., Krause, T. R. & Rathke, J.W. 1988 Silane-silanol dehydrocondensation. The microscopic reverse of hydrogen activation by an organometallic oxide complex, J. Organomet. Chem. 352, 81-94.
    • (1988) J. Organomet. Chem. , vol.352 , pp. 81-94
    • Klingler, R.J.1    Krause, T.R.2    Rathke, J.W.3
  • 8
    • 0000796433 scopus 로고
    • Dynamic stereochemistry at silicon
    • chapt 4 in Patai S. & Rappoport E. (Eds.), John Wiley & Sons, New York; (b) Corriu R.J.P., Guerin C., Moreau J.J.E. 1984 Top. Stereochem. 15, 43
    • (a) Corriu R.J.P., Guerin C. & Moreau J.J.E. 1989 Dynamic stereochemistry at silicon, chapt 4, p 305-370 in The Chemistry of Organic Silicon Compounds, Part I, Patai S. & Rappoport E. (Eds.), John Wiley & Sons, New York; (b) Corriu R.J.P., Guerin C., Moreau J.J.E. 1984 Top. Stereochem. 15, 43.
    • (1989) The Chemistry of Organic Silicon Compounds, Part I , pp. 305-370
    • Corriu, R.J.P.1    Guerin, C.2    Moreau, J.J.E.3
  • 9
    • 0001594362 scopus 로고    scopus 로고
    • A stereoselective approach to optically active bifunctional 1,3-Dimethyl-1,3-diphenyldisiloxanes
    • Oishi, M. & Kawakami, Y. 1999 A stereoselective approach to optically active bifunctional 1,3-Dimethyl-1,3-diphenyldisiloxanes, Org. Lett. 1, 549-552.
    • (1999) Org. Lett. , vol.1 , pp. 549-552
    • Oishi, M.1    Kawakami, Y.2
  • 10
    • 0035110021 scopus 로고    scopus 로고
    • Synthesis of poly(methylphenylsiloxane) rich in syndiotacticity by Rh-catalyzed stereoselective cross-dehydrocoupling polymerization of optically active 1,3-Dimethyl-1,3-diphenyldisiloxane derivatives
    • (a) (b) Oishi, M. & Kawakami, Y. 2000 Synthesis of stereoregular and optically active polysiloxanes containing 1,3-Dimethyl-1,3-diphenyldisiloxane as a constitutional unit, Macromolecules 33, 1960-1963; (c) Seino, M., Oishi, M., Imae, I. & Kawakami, Y. 2002 Formation of poly(silsesquioxane) gel containing optically active 1,3-Dimethyl-1,3-diphenyldisiloxane as a connecting unit', Polym. J. 34, 43-47
    • (a) Oishi, M., Moon, J. Y., Janvikul, W. & Kawakami, Y. 2001 Synthesis of poly(methylphenylsiloxane) rich in syndiotacticity by Rh-catalyzed stereoselective cross-dehydrocoupling polymerization of optically active 1,3-Dimethyl-1,3-diphenyldisiloxane derivatives, Polym. Int. 50, 135-143; (b) Oishi, M. & Kawakami, Y. 2000 Synthesis of stereoregular and optically active polysiloxanes containing 1,3-Dimethyl-1,3-diphenyldisiloxane as a constitutional unit, Macromolecules 33, 1960-1963; (c) Seino, M., Oishi, M., Imae, I. & Kawakami, Y. 2002 Formation of poly(silsesquioxane) gel containing optically active 1,3-Dimethyl-1,3-diphenyldisiloxane as a connecting unit', Polym. J. 34, 43-47.
    • (2001) Polym. Int. , vol.50 , pp. 135-143
    • Oishi, M.1    Moon, J.Y.2    Janvikul, W.3    Kawakami, Y.4
  • 11
    • 14644434745 scopus 로고    scopus 로고
    • Formation of siloxane bonds via new condensation process
    • (a) (b) Zhou, D.Q. & Kawakami, Y. 2005 Tris(pentafluorophenyl)borane as a superior catalyst in the synthesis of optically active SiO-containing polymers, Macromolecules 38, 6902-6908; (c) Chojnowski, J., Rubinsztajn, S., Cella, J.A., Fortuniak, W., Cypryk, M., Kurjata, J. & Kazmierski, K. 2005 Mechanism of the B(C 6 F 5) 3 -catalyzed reaction of silyl hydrides with alkoxysilanes. Kinetic and spectroscopic studies, Organometallics 24, 6077-6084
    • (a) Rubinsztajn, S. & Cella, J.A. 2004 Formation of siloxane bonds via new condensation process. Polym. Preprints 45, 635-636; (b) Zhou, D.Q. & Kawakami, Y. 2005 Tris(pentafluorophenyl)borane as a superior catalyst in the synthesis of optically active SiO-containing polymers, Macromolecules 38, 6902-6908; (c) Chojnowski, J., Rubinsztajn, S., Cella, J.A., Fortuniak, W., Cypryk, M., Kurjata, J. & Kazmierski, K. 2005 Mechanism of the B(C 6 F 5) 3 -catalyzed reaction of silyl hydrides with alkoxysilanes. Kinetic and spectroscopic studies, Organometallics 24, 6077-6084.
    • (2004) Polym. Preprints , vol.45 , pp. 635-636
    • Rubinsztajn, S.1    Cella, J.A.2
  • 12
    • 33947467174 scopus 로고
    • Optically active organosilicon compounds having reactive groups bonded to asymmetric silicon. Displacement reactions at silicon with pure retention and pure inversion of configuration
    • Sommer, L.H. & Frye, C.L. 1959 Optically active organosilicon compounds having reactive groups bonded to asymmetric silicon. Displacement reactions at silicon with pure retention and pure inversion of configuration, J. Am. Chem. Soc. 81, 1013.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1013
    • Sommer, L.H.1    Frye, C.L.2
  • 13
    • 0011491132 scopus 로고
    • Preparation, resolution and dynamic stereochemistry of the 7H-7-Methyl-7-Silabenz[d,e] anthracene system
    • Citron, J.D. 1975 Preparation, resolution and dynamic stereochemistry of the 7H-7-Methyl-7-Silabenz[d,e] anthracene system, J. Organomet. Chem. 86, 359-367.
    • (1975) J. Organomet. Chem. , vol.86 , pp. 359-367
    • Citron, J.D.1
  • 14
    • 84984933281 scopus 로고    scopus 로고
    • Synthesis of optically active allylhydromethylphenylsilane and elucidation of the stereochemical pathway to give isotactic poly(methylphenylsilylenetrimethylene)
    • (a) (b) Kawakami, Y. & Imae, I. 1999 Functionality and stereochemical design of silicon-containing polymers, Macromol. Chem. Phys. 200, 1245-1256
    • (a) Kawakami, Y., Takahashi, T., Yada, Y. & Imae, I. 1998 Synthesis of optically active allylhydromethylphenylsilane and elucidation of the stereochemical pathway to give isotactic poly(methylphenylsilylenetrimethylene), Polym. J. 30, 1001-1003; (b) Kawakami, Y. & Imae, I. 1999 Functionality and stereochemical design of silicon-containing polymers, Macromol. Chem. Phys. 200, 1245-1256.
    • (1998) Polym. J. , vol.30 , pp. 1001-1003
    • Kawakami, Y.1    Takahashi, T.2    Yada, Y.3    Imae, I.4
  • 15
    • 0035111922 scopus 로고    scopus 로고
    • Chromatographic separation of asymmetric organosilicon compounds on cellulose and amylose stationary phases. The stereochemistry of functional transformation reactions
    • Shinke, S. & Kawakami, Y. 2001 Chromatographic separation of asymmetric organosilicon compounds on cellulose and amylose stationary phases. The stereochemistry of functional transformation reactions, Chromatographia 53, 140-146.
    • (2001) Chromatographia , vol.53 , pp. 140-146
    • Shinke, S.1    Kawakami, Y.2
  • 16
    • 0034685977 scopus 로고    scopus 로고
    • 3- catalyzed hydrosilation of carbonyl functions
    • 3-catalyzed silation of alcohols: A mild, general method for synthesis of silyl ethers, J. Org. Chem. 64, 4887-4892
    • 3-catalyzed silation of alcohols: A mild, general method for synthesis of silyl ethers, J. Org. Chem. 64, 4887-4892.
    • (2000) J. Org. Chem. , vol.65 , pp. 3090-3098
    • Parks, D.J.1    Blackwell, J.M.2    Piers, W.E.3


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