Abstract
Here we describe simple and efficient double Michael additions of aromatic and aliphatic methyl ketones to electron deficient alkenes promoted on a surface of KF-alumina. This one-pot procedure provides an easy access to a host of functionalized pimelate esters, which can be subsequently converted in to 3-acylcyclohexanones.
Key words
double Michael additions - acetophenone - KF-alumina - pimelate esters - cyclohexanones
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Representative Experimental Procedure: A mixture of 4-methoxyacetophenone (300 mg, 2 mmol) and ethyl acrylate (600 mg, 6 mmol) was added in one portion to dry preformed KF-alumina (2 g) and the solid mixture was stirred at 60 °C for 10 h. TLC was checked and the mixture was packed on a column of silica gel and eluted with petroleum ether-EtOAc (9:1) to afford diethyl (4-methoxybenzoyl) heptanedioate as colorless viscous oil (553 mg, 79%). IR (neat): 1735, 1680, 1588 cm-1 . 1 H NMR (300 MHz, CDCl3 ): δ = 1.22 (t, 6 H, J = 7.1 Hz, 2 OCH2 CH
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