3-Alkyl-3-chloro-4-chloromethyl-g-lactones were synthesized in acceptable yields, exploiting the CuCl- N,N,N0 ,N00 ,N00-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 g-lactol and final oxidation to lactone with Jones’ reagent.
Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-gamma-lactones
PETRILLO, GIOVANNI;SANCASSAN, FERNANDO;
2009-01-01
Abstract
3-Alkyl-3-chloro-4-chloromethyl-g-lactones were synthesized in acceptable yields, exploiting the CuCl- N,N,N0 ,N00 ,N00-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 g-lactol and final oxidation to lactone with Jones’ reagent.
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