1.1: 95 percent / n-butylboronic complex of diphenyl D-prolinol; catecholborane / toluene / 36 h / -78 °C 2.1: 97 percent / Et3N; imidazole / dimethylformamide / 20 °C 3.1: n-BuLi; CuCN; MeLi / diethyl ether / 3.08 h / -78 - 0 °C 3.2: diethyl ether; hexane / 0.33 h / -78 °C 4.1: pyridinium p-toluenesulfonate / acetone; H2O / 4 h / 20 °C 5.1: 89 percent / porcine pancreatic lipase; NaCl; CaCl2 / H2O; tetrahydrofuran / 0.5 h / Enzymatic reaction; pH 7.1 View Scheme

aluminium trichloride; sodium iodide in acetone 1 h; Heating;

sodium iodide in trifluoroacetic acid 0.5 h; Ambient temperature;

sodium iodide in acetone

aluminium trichloride; sodium iodide in acetone

trimethylsilyl iodide; titanium tetrachloride in dichloromethane T=-78°C;

sodium iodide in acetic acid 0.5 h; Ambient temperaturevarious acetylenic ketones, iodinating reagents, solvents and reaction conditions; Product distribution;

benzo[1,3,2]dioxaborole; Oxazaborolidine 2 in toluene T=-78°C; 15 h;

binaphthol-modified lithium aluminum hydride lt;(S)-6gt; Yield given. Yields of byproduct given;

magnesium