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As the atropisomer 1t-B, separated by preparative HPLC, contains a small amount of 1t-A (ca. 5%), the intrinsic activity of 1t-B is presumed to be weaker than that shown in Table 1.
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note
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We also attempted the methylation (at -60 °C) of the secondary amides (racemic) having 3,5-dimethoxy groups and 4-trifluoromethyl group in place of 7 (and 8) and observed the steric effect of the substituent(s) at the benzylic phenyl on the selectivity; the former gave the diastereomers [(aR*,S*):(aS*,S*)] in a ratio of ca. 2:3, while the latter showed stereoselectivity to afford the diastereomers [(aR*,S*):(aS*,S*)] in a ratio of ca. 5:1, suggesting that the meta-substitution(s) would have a deleterious steric effect on the selectivity.
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25
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15644370681
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Circular dichroism data of the N-salicylidene derivatives prepared in situ
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Circular dichroism data of the N-salicylidene derivatives prepared in situ.
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26
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0001353331
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