methanol; sodium methylate T=60°C; 16 h; Product distribution / selectivity;

lithium hydroxide; water in tetrahydrofuran; methanol T=20°C; Product distribution / selectivity;

triethylsilane; boron trifluoride diethyl etherate in anhydrous dichloroethane T=-30 - 20°C; 1.5 - 2 h; Product distribution / selectivity;

triethylsilane; boron trifluoride diethyl etherate in dichloromethane Inert atmosphereCooling with acetone-dry iceCooling with ice; enantioselective reaction;

1.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20.5 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere 2.2: 0 °C / pH 7 - 8 3.1: n-butyllithium; zinc dibromide / n-heptane; toluene; anhydrous butyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 3.2: 6.5 h / 95 °C 4.1: methanol / sodium methylate / 16 h / 60 °C View Scheme

1.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere 1.2: 0 °C / pH 7 - 8 2.1: n-butyllithium; zinc dibromide / n-heptane; toluene; anhydrous butyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 2.2: 6.5 h / 95 °C 3.1: methanol / sodium methylate / 16 h / 60 °C View Scheme

1.1: n-butyllithium; zinc dibromide / n-heptane; toluene; anhydrous butyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 1.2: 6.5 h / 95 °C 2.1: methanol / sodium methylate / 16 h / 60 °C View Scheme

1.1: (trimethyl)silylmethyllithium / toluene; diethyl ether; pentane / 0.75 h / -50 °C / Inert atmosphere 1.2: 1 h / 25 °C 2.1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme

1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 2: methanol / 16 h / 20 - 60 °C 3: water / 1 h / 0 °C View Scheme

1.1: 1H-imidazole / tetrahydrofuran / 0 °C 2.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / |Reflux 2.2: 1 h / 20 °C 2.3: 5 h / 20 - 150 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C View Scheme