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(a) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
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Myers, A.G.1
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(b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
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Myers, A.G.1
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Gleason, J.L.6
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The desired S-configuration for alcohol 5a originates in the alkylation reaction. According to Myers,4b the newly introduced alkyl chain is attached from the side which comprises the methyl substituent of the pseudoephedrine side chain. We measured the optical rotation for (S)-5a to be [α]D20-11.8 (c 1.00, CHCl3, In the literature the value for the enantiomer (R)-5a was published as [α]D24+9.04 (c 1.2, CHCl3).15 The opposite signs illustrate that these compounds are enantiomers and the higher value for our compound is due to its higher optical purity. Additionally, the absolute configuration of the oxoamide precursor, 2S),1′S)-6a, which was converted into alcohol (S)-5a, was determined by X-ray diffraction.11
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38849133721
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2O. Daicel Chiralpak® IA columns (n-hexane-2-propanol, 99:1) were used for the analytical and semi-preparative HPLC separation.
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2O. Daicel Chiralpak® IA columns (n-hexane-2-propanol, 99:1) were used for the analytical and semi-preparative HPLC separation.
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2) columns. Epimeric mixtures of the hydroxyamides were used as standards; they were synthesized from racemic 2-substituted carboxylic acids, activated as acid chlorides, and reacted with (+)-(1S,2S)-pseudoephedrine.
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2) columns. Epimeric mixtures of the hydroxyamides were used as standards; they were synthesized from racemic 2-substituted carboxylic acids, activated as acid chlorides, and reacted with (+)-(1S,2S)-pseudoephedrine.
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38849184826
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Yields for the alkylation correspond to those published in the experimental section. The yields for the reduction of hydroxyamides 4a-f directly to the alcohols originate in unpublished results (L. F. Tietze, C. Raith).
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Yields for the alkylation correspond to those published in the experimental section. The yields for the reduction of hydroxyamides 4a-f directly to the alcohols originate in unpublished results (L. F. Tietze, C. Raith).
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13 All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in the model. CCDC-664393 [(-)-(2S,1′S)-6a] contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Cyrstallographic Data Centre via www.ccdc.ac.uk/data_request/cif.
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13 All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in the model. CCDC-664393 [(-)-(2S,1′S)-6a] contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Cyrstallographic Data Centre via www.ccdc.ac.uk/data_request/cif.
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Tsuda, K.; Kishida, Y.; Hayatsu, R. J. Am. Chem. Soc. 1960, 82, 3396.
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Tsuda, K.1
Kishida, Y.2
Hayatsu, R.3
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