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Reaction Conditions:

Stage #1: cyclohexenone;methyllithiumwith lithium bromide in 2-methyltetrahydrofuran;diethyl ether at 0; for 2 h;
Stage #2: with ammonium chloride in 2-methyltetrahydrofuran;diethyl ether;water at 0;regioselective reaction;

Steps:

4.3. General procedure for LiBr mediated 1,2-addition of different organolithiums in 2-MeTHF to α,β-unsaturated compounds

General procedure: In a typical experiment a mixture of α,β-unsaturated compound (2.00 mmol, 1.0 equiv) and LiBr (3.00 mmol, 1.5 equiv) in freshly distilled 2-MeTHF (5 mL) was cooled at 0 °C. Organolithium reagents (3.00 mmol, 1.5 equiv) were then added drop-wise. After 2 h, reactions were quenched with saturated ammonium chloride aqueous solution (5 mL). After extraction with ethyl acetate (2×10 mL), desiccation over sodium sulfate, filtration, and solvent removal under reduced pressure, whenever necessary, the crude products were purified by liquid chromatography.

References:

Pace, Vittorio;Castoldi, Laura;Hoyos, Pilar;Sinisterra, José Vicente;Pregnolato, Massimo;Sánchez-Montero, Ma. José [Tetrahedron,2011,vol. 67,# 14,p. 2670 - 2675] Location in patent:supporting information; experimental part

930-68-7
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