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All the reported ring-opened epoxide derivatives gave analytical and spectroscopic data in agreement with the proposed structures.
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The fact that 15 reacts under these conditions establishes a marked contrast with the previously noticed unreactivity of alkyl-substituted terminal epoxides in copper(II)-catalyzed opening reaction in the presence of acetone at 60 °C; see: Hanzlik, R. P.; Leinwetter, M. J. Org. Chem. 1978, 43, 438-440.
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2-promoted reaction, the amino alcohol derivative obtained also holds a trans relationship for these two functional groups; however, the opposite regioisomer was formed. See: Kauffman, G. S.; Harris, G. D.; Dorow, R. L.; Stone, B. R. P.; Parsons Jr., R. L.; Pesti, J. A.; Magnus, N. A.; Fortunak, J. M.; Confalone, P. N.; Nugent, W. A. Org. Lett. 2000, 2, 3119-3121.
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For the first examples of intermolecular kinetic resolution of epoxides with alcohols catalyzed by metal complexes, see: Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688. For related recent work, see: Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
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For the first examples of intermolecular kinetic resolution of epoxides with alcohols catalyzed by metal complexes, see: Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688. For related recent work, see: Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
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