163913-93-7Relevant articles and documents
Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid
Pearson, Neil D.,Broom, Nigel J.P.,O'Hanlon, Peter J.
, p. 3771 - 3774 (2007/10/02)
Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave α-alkylated products (5). This alkylation procedure was surprisingly catalysed by 4- dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced the E-isomer (7). Deprotection gave the monic acid derived ketone (1).