TY - JOUR
T1 - Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-gamma-lactones
AU - Ghelfi, Franco
AU - Roncaglia, Fabrizio
AU - Pattarozzi, Mariella
AU - Giangiordano, Valerio
AU - Petrillo, Giovanni
AU - Sancassan, Fernando
AU - Parsons, Andrew F.
PY - 2009/12/12
Y1 - 2009/12/12
N2 - 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.
AB - 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.
KW - ALPHA-IODO ESTERS
KW - SYNTHETIC ROUTE
KW - ALPHA,ALPHA-DICHLORO ESTERS
KW - INTRAMOLECULAR CYCLIZATIONS
KW - FUNCTIONAL REARRANGEMENT
KW - CONFORMATIONAL-ANALYSIS
KW - COPPER-COMPLEXES
KW - LIGAND STRUCTURE
KW - N-HETEROCYCLES
KW - ATRC REACTIONS
UR - http://www.scopus.com/inward/record.url?scp=70350738990&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2009.10.053
DO - 10.1016/j.tet.2009.10.053
M3 - Article
SN - 0040-4020
VL - 65
SP - 10323
EP - 10333
JO - Tetrahedron
JF - Tetrahedron
IS - 50
ER -