ruthenium trichloride; sodium periodate in tetrachloromethane; acetonitrile

1: D-cis-4,5-methanoprolineamide methanesulfonic acid salt With sodium ethanolate in ethanol; isopropyl alcohol T=50°C; 1 h; 2: With water in ethanol; isopropyl alcohol T=60°C; 18 h; 3: di-tert-butyl dicarbonate in ethanol; water; isopropyl alcohol

sodium periodate; ruthenium trichloride in tetrachloromethane; water; acetonitrile 1.25 h;

sodium periodate; water; ruthenium trichloride in tetrachloromethane; acetonitrile 1.25 h;

ruthenium trichloride; sodium periodate in tetrachloromethane; water; acetonitrile 1.25 h;

2: 90 percent / TBAF / tetrahydrofuran 3: 75 percent / aq. NaIO4, RuCl3 / CCl4; acetonitrile View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 18.16 h / 24 °C 2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -50 - -45 °C 2.2: 14.42 h / -50 - 20 °C 2.3: 0.08 h / Cooling with ice/water 3.1: diethylzinc / toluene / 0.25 h / -30 °C 3.2: 19.66 h / -25 - -21 °C 3.3: 0.33 h / -25 - 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.83 h / 20 °C 5.1: sodium periodate; ruthenium trichloride / tetrachloromethane; acetonitrile; water / 1.25 h View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 20 °C 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 18.16 h / 24 °C 3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -50 - -45 °C 3.2: 14.42 h / -50 - 20 °C 3.3: 0.08 h / Cooling with ice/water 4.1: diethylzinc / toluene / 0.25 h / -30 °C 4.2: 19.66 h / -25 - -21 °C 4.3: 0.33 h / -25 - 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.83 h / 20 °C 6.1: sodium periodate; ruthenium trichloride / tetrachloromethane; acetonitrile; water / 1.25 h View Scheme

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 72 h / 10 - 20 °C 2.1: sodium tetrahydroborate / ethanol / 17 h / 10 - 12 °C 2.2: pH ~ 3 3.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 0 - 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 8 h / 20 °C 5.1: lithium triethylborohydride / toluene; tetrahydrofuran / -55 - -47 °C 5.2: -50 - -47 °C 5.3: 16 h / -52 - 20 °C 6.1: diethylzinc / toluene / 20 h / -35 - -21 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C 8.1: sodium periodate / ruthenium trichloride / tetrachloromethane; acetonitrile; water / 2 h / 18 - 24 °C View Scheme

1.1: sodium tetrahydroborate / ethanol / 17 h / 10 - 12 °C 1.2: pH ~ 3 2.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 0 - 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 8 h / 20 °C 4.1: lithium triethylborohydride / toluene; tetrahydrofuran / -55 - -47 °C 4.2: -50 - -47 °C 4.3: 16 h / -52 - 20 °C 5.1: diethylzinc / toluene / 20 h / -35 - -21 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C 7.1: sodium periodate / ruthenium trichloride / tetrachloromethane; acetonitrile; water / 2 h / 18 - 24 °C View Scheme