diethylzinc; RhCl(PPh3)3 in tetrahydrofuran; hexane T=0°C; Cyclization; Reformatsky-type reaction; 0.0833333 h;

zinc(II) tetrahydroborate in diethyl ether T=0°C; 0.5 h;

1: 83 percent / PCC; sodium acetate; 4 Angstroem MS / CH2Cl2 / 1 h / 20 °C 2: 63 percent / Et2Zn / RhCl(PPh3)3 / tetrahydrofuran; hexane / 0.08 h / 0 °C View Scheme

1.1: LDA; chlorotrimethylsilane / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: NBS / tetrahydrofuran; hexane / 1 h / 0 °C 2.1: 797 mg / p-TsOH*H2O / ethanol / 2 h / 0 °C 3.1: 83 percent / PCC; sodium acetate; 4 Angstroem MS / CH2Cl2 / 1 h / 20 °C 4.1: 63 percent / Et2Zn / RhCl(PPh3)3 / tetrahydrofuran; hexane / 0.08 h / 0 °C View Scheme

1: 797 mg / p-TsOH*H2O / ethanol / 2 h / 0 °C 2: 83 percent / PCC; sodium acetate; 4 Angstroem MS / CH2Cl2 / 1 h / 20 °C 3: 63 percent / Et2Zn / RhCl(PPh3)3 / tetrahydrofuran; hexane / 0.08 h / 0 °C View Scheme

1.1: 99 percent / triethylamine / CH2Cl2 / 2 h / 20 °C 2.1: LDA; chlorotrimethylsilane / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: NBS / tetrahydrofuran; hexane / 1 h / 0 °C 3.1: 797 mg / p-TsOH*H2O / ethanol / 2 h / 0 °C 4.1: 83 percent / PCC; sodium acetate; 4 Angstroem MS / CH2Cl2 / 1 h / 20 °C 5.1: 63 percent / Et2Zn / RhCl(PPh3)3 / tetrahydrofuran; hexane / 0.08 h / 0 °C View Scheme

sodium hydroxide unter starker Kuehlung und sofortigem Ansaeuern der Reaktionsloesung mit Schwefelsaeure;

nickel; ethyl acetate Hydrogenation;

/BRN= 3195777/;

Candida antarctica lipase B; water in tert-butyl methyl ether T=30°C; 1 h; Resolution of racemateEnzymatic reaction; Reagent/catalystSolventTemperature; enantioselective reaction;