Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane

CECILIA A. BARRIONUEVO; LUCIANA C. SCHMIDT; JUAN E. ARGÜELLO

NEW JOURNAL OF CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2016

1144-0546

yclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as reagent followed by a subsequent double alkylation with the bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C-C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions