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

Abstract α-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct α-chlorinated medium-size cyclic ketones. This intermolecular Tiffeneau–Demjanov reaction proceeds in good yield from easily prepared or commercially available startin...

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Veröffentlicht in:	Synthesis (Stuttgart) 2016-08, Vol.48 (15), p.2396-2401
Hauptverfasser:	Dousset, Maxime, Le Jeune, Karel, Cohen, Sylvana, Parrain, Jean-Luc, Chouraqui, Gaëlle
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Sprache:	eng
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description	Abstract α-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct α-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.
doi_str_mv	10.1055/s-0035-1561413
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title	Tiffeneau–Demjanov Rearrangement by Using α-Chloro-α-diazoacetate: A Direct Access to α-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement
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