dimethylsulfide; borane in tetrahydrofuran T=25°C; 48 h;

in tetrahydrofuran; water 9 h; Ambient temperature;

sodium tetrahydroborate; lithium chloride in tetrahydrofuran; ethanol T=20°C; 3 h;

1: NaBH4; I2 / tetrahydrofuran / 18 h 2: pyridine / -30 - 0 °C View Scheme

potassium hydrogencarbonate in methanol T=20°C; 0.166667 h;

sodium carbonate in tetrahydrofuran; water T=0 - 20°C; 3 h; stereoselective reaction;

1: (2R,4S)-3-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-1,2,3-oxathiazolidine 2-oxide; 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran T=-68°C; Inert atmosphereCooling with acetone-dry ice; 2: With lithium hexamethyldisilazane in tetrahydrofuran T=-68 - 20°C; Inert atmosphere; 3: benzaldehyde With titanium tetraethoxide in tetrahydrofuran T=20°C; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1: 85 percent / 1.5 N NaOH / diethyl ether / 6 h / 25 °C 2: 98 percent / borane-dimethyl sulfide complex / tetrahydrofuran / 48 h / 25 °C View Scheme

1: (S)-(-)-2-amino-3-phenyl-1-propanol in acetonitrile T=20°C; Electrolysis; 2: carbon dioxide 1 h; 3: p-toluenesulfonyl chloride T=20°C;

1: triethylamine / dichloromethane / 0 - 25 °C 2: lithium borohydride / tetrahydrofuran / 0 - 20 °C View Scheme