Unprecedented use of 29Si NMR spectroscopy for a convenient determination of enantiomeric excesses of chiral α-C-silylated amines and alcohols

Chemical Communications

Volumn , Issue 6, 1999, Pages 527-528

  Fortis, Frederic ^a   Barbe, Bernard ^a   Pétraud, Michel ^a   Picard, Jean Paul ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; LANTHANIDE; ORGANOSILICON DERIVATIVE; SILICON;

ARTICLE; CHIRALITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0033590757     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900491b     Document Type: Article

References (36)

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12. See for examples: R. J. Fessenden and M. D. Coon, J. Med. Chem., 1964, 7, 561; M. Kurono, R. Unno, Y. Matsumoto, Y. Kondo, T. Mitani, T. Jomori, H. Michishita and K. Sawai, Eur. Pat. Appl. EP 288,002 1988 (Chem. Abstr., 1989, 110, 75808); M. Kurono, T. Suzuki, T. Suzuki, K. Hirooka, Y. Matsumoto, H. Ozawa and K. Sawai, Eur. Pat. Appl. EP 299,495 1989 (Chem. Abstr., 1989, 111, 7217); R. Tacke, R. Niedner, J. Frohnecke, L. Ernst and W. S. Sheldrick, Liebigs Ann. Chem., 1980, 1859; R. B. Silverman and G. M. Banik, J. Am. Chem. Soc., 1987, 109, 2219. G. M. Banik, R. B. Silverman, J. Am. Chem. Soc., 1990, 112, 4499.
13. See for examples: R. J. Fessenden and M. D. Coon, J. Med. Chem., 1964, 7, 561; M. Kurono, R. Unno, Y. Matsumoto, Y. Kondo, T. Mitani, T. Jomori, H. Michishita and K. Sawai, Eur. Pat. Appl. EP 288,002 1988 (Chem. Abstr., 1989, 110, 75808); M. Kurono, T. Suzuki, T. Suzuki, K. Hirooka, Y. Matsumoto, H. Ozawa and K. Sawai, Eur. Pat. Appl. EP 299,495 1989 (Chem. Abstr., 1989, 111, 7217); R. Tacke, R. Niedner, J. Frohnecke, L. Ernst and W. S. Sheldrick, Liebigs Ann. Chem., 1980, 1859; R. B. Silverman and G. M. Banik, J. Am. Chem. Soc., 1987, 109, 2219. G. M. Banik, R. B. Silverman, J. Am. Chem. Soc., 1990, 112, 4499.
14. See for examples: R. J. Fessenden and M. D. Coon, J. Med. Chem., 1964, 7, 561; M. Kurono, R. Unno, Y. Matsumoto, Y. Kondo, T. Mitani, T. Jomori, H. Michishita and K. Sawai, Eur. Pat. Appl. EP 288,002 1988 (Chem. Abstr., 1989, 110, 75808); M. Kurono, T. Suzuki, T. Suzuki, K. Hirooka, Y. Matsumoto, H. Ozawa and K. Sawai, Eur. Pat. Appl. EP 299,495 1989 (Chem. Abstr., 1989, 111, 7217); R. Tacke, R. Niedner, J. Frohnecke, L. Ernst and W. S. Sheldrick, Liebigs Ann. Chem., 1980, 1859; R. B. Silverman and G. M. Banik, J. Am. Chem. Soc., 1987, 109, 2219. G. M. Banik, R. B. Silverman, J. Am. Chem. Soc., 1990, 112, 4499.
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35. 29Si NMR spectrum (39.76 MHz) was collected (256 scans) at 300 K on a Bruker Avance DPX 200 MHz spectrometer over a spectral width of 7961 Hz with a repetition delay of 1 s between scans to allow for complete relaxation. INEPT delay time parameters choosen were τ = 0.0357 s and Δ = 0.02 s. Slight line Gaussian multiplication (-0.1 Hz) was applied to aid resolution. The FIDs were Fourier transformed and phased automatically, the same phase corrections being applied for each sample. Integration gave the relative proportions of the diastereoisomeric complexes as listed in Table 1.
36. See Table 1, Experiment 1 in ref 6.