Tetrahedron letters

Preparation of E-(2-substituted-1-methylethylidene) indanones derived from monic acid

ND Pearson, NJP Broom, PJ O'Hanlon

Index: Pearson, Neil D.; Broom, Nigel J.P.; O'Hanlon, Peter J. Tetrahedron Letters, 1994 , vol. 35, # 22 p. 3771 - 3774

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Citation Number: 4

Abstract

Abstract 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 ...