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33644990789
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SAR results will be published and discussed elsewhere in due course.
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44
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33644973370
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note
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3, reflux, 22 h (xylene) 78% (two steps)).
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45
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33644981757
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See Ref. 3a.
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A similar isomerization of the corresponding methylsulfone has been reported by Corbett et al. In that case, the stronger electron-withdrawing effect of the sulfone as compared to the bromide apparently increased the rate of isomerization such that treatment with methanolic aqueous base at rt for 20 h resulted in complete isomerization without competing saponification. Subsequent removal of methanol and brief heating afforded the E-carboxylic acid exclusively. When these conditions were applied to the bromide, a mixture of E/Z carboxylic acids was obtained. See Ref. 3a.
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46
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33644978057
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note
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HPLC was done using a 80 mm ID dynamic axial compression (DAC) Novasep column separating up to 24 g/h of the racemic cyclopropyl alcohol. Conditions: 1 kg Daicel Chiralpak AD (20 μm), mobile phase: 100% MeCN, starting flow rate 150 ml/min, end run flow rate 320 ml/min, 260 nm.
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50
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33644985174
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note
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All experimental procedures were similar to those in cited references and any differences are included in stated exp. details.
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