1: With titanium tetrachloride in dichloromethane T=20°C; Aldol Condensation; 0.666667 h; Inert atmosphere; 2: With triethylamine in dichloromethane T=20 - 30°C; Aldol Condensation; Inert atmosphere; stereoselective reaction;

diisopropylamine in tetrahydrofuran; hexane; water

sodium tetrahydroborate in ethanol T=-78°C; 18 h; Title compound not separated from byproducts;

1: (diethoxy-phosphoryl)-fluoro-acetic acid ethyl ester With n-butyllithium in tetrahydrofuran; hexane T=0°C; 1 h; 2: pivalaldehyde in tetrahydrofuran; hexane T=0 - 20°C; Horner-Wadsworth-Emmons reaction; Title compound not separated from byproducts;

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C 1.2: 60 percent / hexane; tetrahydrofuran / 1 h / 0 °C 2.1: NaBH4 / ethanol / 18 h / -78 °C View Scheme