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Volumn 28, Issue 20, 2009, Pages 6059-6066

Asymmetric synthesis of the nonproteinogenic silicon-containing α-amino acids (R)- And (5)-α-[(trimethylsilyl)methyl] alanine

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ASYMMETRIC SYNTHESIS; CRYSTAL STRUCTURE ANALYSIS; DIETHYL MALONATES; ENANTIOMERIC PURITY; ENANTIOSELECTIVE; MALONATES; MULTI-STEP; PORCINE LIVER ESTERASE; PROPANOIC ACID; RHODIUM COMPLEXES; TRIMETHYLSILYL;

EID: 70350317339     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900583d     Document Type: Article
Times cited : (12)

References (52)
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    • Tacke, R.1    Wagner, S.A.2
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    • note
    • 29Si).
  • 37
    • 70350260016 scopus 로고    scopus 로고
    • 1H NMR spectroscopy), the intermediate ethyl rac-3-azido-2-methyl-3oxo-2- [(trimethylsilyl)methyl]propanoate was not isolated
    • 1H NMR spectroscopy), the intermediate ethyl rac-3-azido-2-methyl-3oxo-2- [(trimethylsilyl)methyl]propanoate was not isolated.
  • 39
    • 70350276606 scopus 로고    scopus 로고
    • note
    • Repeated recrystallization of (S)-13 from n-hexane at -20 °C yielded a product with an enantiomeric purity of > 99% ee; however, the yield was very poor. The melting point and the specific optical rotation given in the Experimental Section refer to the recrystallized product (>99%ee).
  • 41
    • 0004048804 scopus 로고    scopus 로고
    • University of Utrecht: Utrecht, The Netherlands
    • The hydrogen-bonding systems were analyzed by using the program system PLA TON: Spek, A. L. PLATON; University of Utrecht: Utrecht, The Netherlands, 2008.
    • (2008) PLATON
    • Spek, A.L.1
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    • The molar ratio takes into account the amount of rac-1 -HCl, (R)-1 HCl, or (S)-1• HCl obtained in the former step
    • The molar ratio takes into account the amount of rac-1 -HCl, (R)-1 HCl, or (S)-1• HCl obtained in the former step.
  • 50
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    • The enantiomeric purity was not determined for this compound, but is supposed to be 85% ee
    • ( 18) The enantiomeric purity was not determined for this compound, but is supposed to be 85% ee.
  • 51
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    • To measure the NMR. spectra of (5)-12, the solvent of the reaction solution (CH2CI2) was removed in vacuo and the residue was dissolved in C&Df
    • To measure the NMR. spectra of (5)-12, the solvent of the reaction solution (CH2CI2) was removed in vacuo and the residue was dissolved in C&Df,.


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