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22244491802
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For representative examples of α-trifluoromethyl piperidines and piperideines preparation, see: (a) Ref. 7
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Spanedda, M.V.1
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0346025405
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For successful application of our methodology in the enantioselective synthesis of an indolizidine alkaloid, see: Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011.
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Ogoshi, H.; Mizushima, H.; Toi, H.; Aoyama, Y. J. Org. Chem. 1986, 51, 2366.
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(b) Plenkiewicz, H.; Dmowski, W.; Lipinski, M. J. Fluorine Chem. 2001, 11, 227.
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Plenkiewicz, H.1
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24
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22244488562
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note
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3 (10 mL) was added and the keto-protected piperidone extracted with ethyl acetate (4 × 30 mL). The combined organic extracts were dried, filtered, and concentrated. The residue was purified by column chromatography using ethyl acetate-cyclohexane as eluent.
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25
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22244486494
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note
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The low yield is due to partial butanal aldol condensation prior to cyclization, leading to a complex reaction mixture.
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26
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22244487811
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note
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All new compounds are fully characterized.
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