sodium chlorite; 2-methyl-but-2-ene in water; tert-butyl alcohol T=20°C; 3 h;

trimethyl tin hydroxide in 1,2-dichloro-ethane T=20°C; Reflux;

1.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C 1.2: 93 percent / Pd(PPh3)4 / tetrahydrofuran / 3 h / 50 °C 2.1: 89 percent / KI / H2O; various solvent(s) / 10 h / 130 °C 3.1: 89 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.75 h / -78 °C 4.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C 4.2: 84 percent / tetrahydrofuran / -70 - 20 °C 5.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 6.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 7.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 7.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 7.3: Et3N / CH2Cl2 8.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 9.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 10.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: 94 percent / imidazole / dimethylformamide / 2 h / 20 °C 2.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C 2.2: 93 percent / Pd(PPh3)4 / tetrahydrofuran / 3 h / 50 °C 3.1: 89 percent / KI / H2O; various solvent(s) / 10 h / 130 °C 4.1: 89 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.75 h / -78 °C 5.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C 5.2: 84 percent / tetrahydrofuran / -70 - 20 °C 6.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 7.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 8.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 8.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 8.3: Et3N / CH2Cl2 9.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 10.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 11.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: 89 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.75 h / -78 °C 2.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C 2.2: 84 percent / tetrahydrofuran / -70 - 20 °C 3.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 4.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 5.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 5.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 5.3: Et3N / CH2Cl2 6.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 7.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 8.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: 89 percent / KI / H2O; various solvent(s) / 10 h / 130 °C 2.1: 89 percent / (i-Bu)2AlH / CH2Cl2; hexane / 0.75 h / -78 °C 3.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C 3.2: 84 percent / tetrahydrofuran / -70 - 20 °C 4.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 5.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 6.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 6.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 6.3: Et3N / CH2Cl2 7.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 8.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 9.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C 1.2: 84 percent / tetrahydrofuran / -70 - 20 °C 2.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 3.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 4.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 4.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 4.3: Et3N / CH2Cl2 5.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 6.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 7.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 1.3: Et3N / CH2Cl2 2.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 3.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 4.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1.1: 93 percent / PCC / CH2Cl2 / 3 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: tetrahydrofuran; hexane / 0.33 h / -78 °C 2.3: Et3N / CH2Cl2 3.1: 92 percent / DDQ / CH2Cl2; H2O / 0.75 h / cooling 4.1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 5.1: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme

1: 92 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 2: 93 percent / 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 3 h / 20 °C View Scheme