1: (S)-(-)-4-benzyl-2-oxazolidinone With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.666667 h; 2: (4S)-4-methylhexanoyl chloride in tetrahydrofuran; hexane T=-78°C; 1.5 h;

1: I2, PPh3, imidazole / diethyl ether; acetonitrile / 0 °C 2: 1.) LDA, 2.) N,N'-dimethylpropyleneurea / 1.) THF, -78 deg C, 50 min, 2.) -78 deg C, 5 min; -42 deg C, 3 h; -42 deg C to room temperature 3: 66 percent / TFA / CH2Cl2 / 1.) 0 deg C, 2.5 h, 2.) room temperature, 2.5 h 4: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 2 h / Ambient temperature 5: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2.5 h; -78 deg C to room temperature View Scheme

1: 1.) LDA, 2.) N,N'-dimethylpropyleneurea / 1.) THF, -78 deg C, 50 min, 2.) -78 deg C, 5 min; -42 deg C, 3 h; -42 deg C to room temperature 2: 66 percent / TFA / CH2Cl2 / 1.) 0 deg C, 2.5 h, 2.) room temperature, 2.5 h 3: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 2 h / Ambient temperature 4: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2.5 h; -78 deg C to room temperature View Scheme

1: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 2 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2.5 h; -78 deg C to room temperature View Scheme

1: 66 percent / TFA / CH2Cl2 / 1.) 0 deg C, 2.5 h, 2.) room temperature, 2.5 h 2: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 2 h / Ambient temperature 3: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2.5 h; -78 deg C to room temperature View Scheme

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