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Tiffeneau–Demjanov Rearrangement by Using alpha-Chloro-diazo-acetate: A Direct Access to alpha-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement

Abstract : alpha-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct alpha-chlorinated medium-size cyclic ketones. This intermolecular Tiffeneau–Demjanov reaction proceeds in good yield from easily prepared or commercially available starting materials and allows the concomitant formation of a tetrasubstituted stereocenter.
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https://hal.archives-ouvertes.fr/hal-01414922
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Submitted on : Monday, December 12, 2016 - 4:38:22 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Maxime Dousset, Karel Le Jeune, Sylvana Cohen, Jean-Luc Parrain, Gaëlle Chouraqui. Tiffeneau–Demjanov Rearrangement by Using alpha-Chloro-diazo-acetate: A Direct Access to alpha-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement. SYNTHESIS, Georg Thieme Verlag, 2016, 48, pp.2396-2401. ⟨10.1055/s-0035-1561413⟩. ⟨hal-01414922⟩

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