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The possibility of epimerization of 4 or 5 to give trans-isomers was considered. In a series of tests, however, 4a/4b mixtures were recovered completely unreacted from basic aqueous conditions, or extensively degraded when treated with t-BuOK/THF at reflux. For a related use of these latter conditions, see: Priego, J.; Flores, P.; Ortiz-Nava, C; Escalante, J. Tetrahedron: Asymmetry 2004, 15, 3545-3549.
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The possibility of epimerization of 4 or 5 to give trans-isomers was considered. In a series of tests, however, 4a/4b mixtures were recovered completely unreacted from basic aqueous conditions, or extensively degraded when treated with t-BuOK/THF at reflux. For a related use of these latter conditions, see: Priego, J.; Flores, P.; Ortiz-Nava, C; Escalante, J. Tetrahedron: Asymmetry 2004, 15, 3545-3549.
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