Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-gamma-lactones

Franco Ghelfi, Fabrizio Roncaglia, Mariella Pattarozzi, Valerio Giangiordano, Giovanni Petrillo, Fernando Sancassan, Andrew F. Parsons

Research output: Contribution to journalArticlepeer-review

Abstract

3-Alkyl-3-chloro-4-chloromethyl-gamma-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 Jones' reagent. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)10323-10333
Number of pages11
JournalTetrahedron
Volume65
Issue number50
DOIs
Publication statusPublished - 12 Dec 2009

Keywords

  • ALPHA-IODO ESTERS
  • SYNTHETIC ROUTE
  • ALPHA,ALPHA-DICHLORO ESTERS
  • INTRAMOLECULAR CYCLIZATIONS
  • FUNCTIONAL REARRANGEMENT
  • CONFORMATIONAL-ANALYSIS
  • COPPER-COMPLEXES
  • LIGAND STRUCTURE
  • N-HETEROCYCLES
  • ATRC REACTIONS

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