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Although not appropriate for the methodology in the present work, the diastereoselective preparation of enol triflates from acetoacetate derivatives using aqueous bases has been recently described: Babinski, D.; Soltani, O.; Frantz, D. E. Org. Lett. 2008, 10, 2901.
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Vinyl triflates 3a, 4, and 5 were surprisingly stable to isolation using silica gel chromatography.
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As opposed to arylethyl halides which would be required for additions involving weak propiolate nucleophiles to form compounds such as 8
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As opposed to arylethyl halides which would be required for additions involving weak propiolate nucleophiles to form compounds such as 8.
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