1: 85 percent / Raney nickel (W-1 activity) / acetone / 6 h / Heating 2: 65 percent / conc. HCl / acetic acid / 6 h / Heating View Scheme

1: iodine; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 3 h / 85 °C 4: hydrogen / Lindlar's catalyst / ethyl acetate / 20 °C / 2068.65 Torr View Scheme

1.1: (-)-sparteine; sec-BuLi / various solvent(s); tetrahydrofuran; cyclohexane / 1 h / -78 °C 1.2: various solvent(s); tetrahydrofuran; cyclohexane / 1 h / -78 °C 2.1: n-BuLi / tetrahydrofuran / 2 h / -78 °C 2.2: 97 percent / tetrahydrofuran / 6 h / 20 °C 3.1: 89 percent / KOH / H2O; dioxane / 24 h / Heating 4.1: trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 83 percent / triethylamine / CH2Cl2 / 24 h / 20 °C 2.1: (-)-sparteine; sec-BuLi / various solvent(s); tetrahydrofuran; cyclohexane / 1 h / -78 °C 2.2: various solvent(s); tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.1: n-BuLi / tetrahydrofuran / 2 h / -78 °C 3.2: 97 percent / tetrahydrofuran / 6 h / 20 °C 4.1: 89 percent / KOH / H2O; dioxane / 24 h / Heating 5.1: trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / 2 h / -78 °C 1.2: 97 percent / tetrahydrofuran / 6 h / 20 °C 2.1: 89 percent / KOH / H2O; dioxane / 24 h / Heating 3.1: trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1: 89 percent / KOH / H2O; dioxane / 24 h / Heating 2: trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C View Scheme

(R,R)-tetraphenyl Ti-TADDOLate; hydrogen; palladium on activated charcoal 1.) toluene, -90 deg C; 2.) toluene, -90 deg C, then -75 deg C, 6 h; 3.) EtOAc, r.t., 4 d; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

sodium nitrite in perchloric acid; water Product distributionMechanism;

sodium nitrite in perchloric acid; water Product distributionMechanism;