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35
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85034523618
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Initial studies employing the tosyl hydrazone did not lead to the desired deprotonation
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Initial studies employing the tosyl hydrazone did not lead to the desired deprotonation.
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36
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85034523944
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The use of tosyl imidazole, a more commonly employed reagent for this type of transformation, led to competitive sulfonation of the secondary hydroxyl after epoxide formation, as well as recovered starting material
-
The use of tosyl imidazole, a more commonly employed reagent for this type of transformation, led to competitive sulfonation of the secondary hydroxyl after epoxide formation, as well as recovered starting material.
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37
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0030784540
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38
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0000180260
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Large-scale preparation of this valuable intermediate was carried out using Jacobsen's kinetic resolution methodology: see: Furrow, M. E.; Schaus. S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 68, 6776.
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41
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85034523416
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Treatment with both chelating and nonchelating Lewis acids only afforded a 2.6-2.2:1 ratio of anti/syn diastereomers
-
Treatment with both chelating and nonchelating Lewis acids only afforded a 2.6-2.2:1 ratio of anti/syn diastereomers.
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42
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33751386025
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(a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
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Keck, G. E.; Wager, C. A.; Wager, T. T.; Savin, K. A.; Covel, J. A.; McLaws, M. D.; Krishnamurthy, D.; Cee, V. Angew. Chem., Int. Ed. 2001, 40, 231.
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Cee, V.8
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46
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85034521883
-
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A 20:1 mixture of diastereomers was obtained. This minor diastereomer resulted from competitive tosylation at the secondary hydroxyl followed by displacement of the tosylate
-
A 20:1 mixture of diastereomers was obtained. This minor diastereomer resulted from competitive tosylation at the secondary hydroxyl followed by displacement of the tosylate.
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-
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47
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85034527618
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The reaction proved sensitive to oxygen on small scale. Use of oxyclear argon improved the reproducibility of the reaction
-
The reaction proved sensitive to oxygen on small scale. Use of oxyclear argon improved the reproducibility of the reaction.
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48
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0032512010
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Paterson, I.; Wallace, D. J.; Oballa, R. M. Tetrahedron Lett. 1998, 39, 8545.
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Paterson, I.1
Wallace, D.J.2
Oballa, R.M.3
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50
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85034527702
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We thank Professor I. Paterson for providing spectroscopic data for the correlation compound
-
We thank Professor I. Paterson for providing spectroscopic data for the correlation compound.
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