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From the same journal

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

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

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

Department/unit(s)

Publication details

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

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.

    Research areas

  • 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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