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A Vicarious One-Pot Transformation of a Fluorocyclitol to a Polycyclitol: Observation of a Formal 4-Fold Axial−Equatorial Epimerization on a Conformationally Locked Scaffold

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https://figshare.com/articles/dataset/A_Vicarious_One_Pot_Transformation_of_a_Fluorocyclitol_to_a_Polycyclitol_Observation_of_a_Formal_4_Fold_Axial_Equatorial_Epimerization_on_a_Conformationally_Locked_Scaffold/2707522
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资源简介:
A conformationally locked fluoropentol undergoes an interesting transformation to (trans,anti,trans,anti,trans)-perhydro-2,3,4a,6,7,8a-naphthalenehexol essentially under conditions of base-induced transesterification. The proposed rationale for the observed metamorphosis involves a nucleophilic displacement of fluoride, and subsequent stereo- and regioselective anti-Fürst−Plattner-type ring-opening of the epoxide thus formed.
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2010-12-03
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