3-Alkyl-3-chloro-4-chloromethyl--lactones were synthesized in acceptable yields, exploiting the CuCl-N,N,N’,N”,N”-pentamethyldiethylenetriamine catalyzed atom transfer radical cyclization (ATRC) of O-allyl-2,2-dichlorohemiacetal acetates, starting materials easily prepared from 2,2-dichloroaldehydes. The oxidation of the intermediate dichloro-2-acetoxytetrahydrofurans was completed in a two step, one-pot procedure: hydrolysis to gamma-lactol and final oxidation to lactone with the Jones’ reagent.
Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-gamma-lactones / Ghelfi, Franco; Roncaglia, Fabrizio; Pattarozzi, Mariella; Giangiordano, Valerio; G., Petrillo; F., Sancassan; A. F., Parsons. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:50(2009), pp. 10323-10333. [10.1016/j.tet.2009.10.053]
Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-gamma-lactones.
GHELFI, Franco;RONCAGLIA, Fabrizio;PATTAROZZI, Mariella;GIANGIORDANO, VALERIO;
2009
Abstract
3-Alkyl-3-chloro-4-chloromethyl--lactones were synthesized in acceptable yields, exploiting the CuCl-N,N,N’,N”,N”-pentamethyldiethylenetriamine catalyzed atom transfer radical cyclization (ATRC) of O-allyl-2,2-dichlorohemiacetal acetates, starting materials easily prepared from 2,2-dichloroaldehydes. The oxidation of the intermediate dichloro-2-acetoxytetrahydrofurans was completed in a two step, one-pot procedure: hydrolysis to gamma-lactol and final oxidation to lactone with the Jones’ reagent.
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