N-ethylmorpholine N-oxide in N,N-dimethyl-formamide r.t., 1 h, 50 deg C, 4 h; Yield given. Yields of byproduct given;

oxalyl dichloride; dimethyl sulfoxide; triethylamine 1) CH2Cl2, 20 min, -65 deg C 2) -65 deg C to r.t., 50 min; Yield given. Multistep reaction;

Vanadium catalyst

1: diethyl ether; phosphorus (III)-bromide / -5 °C 2: aqueous KOH-solution; propan-2-ol View Scheme

1: diethyl ether; phosphorus (III)-bromide / -5 °C 2: aqueous KOH-solution; propan-2-ol View Scheme

potassium hydroxide; isopropyl alcohol

potassium cyanide; manganese(IV) oxide; acetic acid T=20°C; 24 h;

1: 77 percent / NaClO2; aq. NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h 2: 76 percent / EDCI / CH2Cl2 / 6 h 3: 73 percent / EDCI; DMAP / CH2Cl2 / 2 h View Scheme

1: 99 percent / NaHMDS / tetrahydrofuran / 2 h / Ambient temperature 2: 1.) BH3, 2-methyl-2-butene, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, 0 deg C, 2 h; room temperature, 12 h, 2.) -10 deg C to room temperature, 3 h 3: 97 percent / PPh3, Br2, pyridine / CH2Cl2 / 1.5 h / 0 °C View Scheme

1: n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 5 h 2: SeO2, 2-hydroxybenzoic acid, 80percent t-BuOOH / CH2Cl2 / 30 h / Ambient temperature 3: 79 percent / 1 M DIBAL / toluene / 0.5 h / -78 °C 4: 95 percent / BaMnO4 / CH2Cl2 / 8 h / Ambient temperature 5: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 6: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 7: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme