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Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes

Abstract : Access to fluoroalkylidene-oxetanes and-azetidines was realized from 3-oxetanone, 3-azetidinone, and fluorosulfones through the Julia-Kocienski reaction. This approach allows the preparation of new precursors of fluorinated four-membered rings that contain a nucleic base, an ester or aryl sulfone function, and a pyrrolidine ring. Benzothiazolyl-sulfonemediated aza-Michael addition reaction of nitrogen nucleophiles enables access to 3,3-disubstituted oxetanes.
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Submitted on : Tuesday, November 12, 2019 - 11:17:15 AM
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Romain Laporte, Anais Prunier, Emmanuel Pfund, Vincent Roy, Luigi Agrofoglio, et al.. Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (14), pp.3121-3128. ⟨10.1002/ejoc.201500172⟩. ⟨hal-02348052⟩

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