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3CN)) suggest that the energy difference between conformers 4A and 4B is ca. 20 kJ, which, if it was translated directly into epoxides, corresponds to 99.8% ee at 40°C).
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35
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3CN)) show that there is a 42° twist of the phenyl group in ylide conformer 4B resulting in reduced stabilization of the ylide carbanion.
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64% Ee is observed for ylide 15 at 40°C, using the Boltzmann equation, it is predicted that the enantioselectivity should be 84% ee at -78°C. However, > 99% ee was actually observed.
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