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34047102706
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3S: C, 66.06, H, 6.71, N, 4.05. Found (%): C, 66.18, H, 6.69, N, 4.25.
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60
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34047174366
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The decreased yield of isolated 1,3-oxazolidine was due to hydrolysis during work-up or column chromatographic purification which was necessary for preparing an analytical sample.
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61
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34047115632
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-1).
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64
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34047123467
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As the reaction of 1 with benzaldehyde approaches rt, the initially formed cis isomer was converted to the trans isomer and the dr (cis:trans) changes to 72:38 (at ∼10 °C). When the reaction was performed in aldehyde medium at rt, the observed dr was 1.22:1.0 (cis:trans). The enantioselectivity of product 3f increased up to 62% when the reaction was carried out at -25 °C. There was no change in ee upon further lowering of the reaction temperature.
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65
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34047111480
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Decrease in ee is probably due to partial racemization of the product at the benzylic position in acidic medium.
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