water; triphenylphosphine; lithium hydroxide hydrate in acetonitrile T=100°C; 0.666667 h; Microwave irradiation; regioselective reaction;

water; sodium hydrogencarbonate; triphenylphosphine in acetonitrile T=100°C; 0.5 h; Microwave irradiation; regioselective reaction;

1: H2O; tetrahydrofuran / 0.25 h / 20 °C 2: NaBH4 / H2O; tetrahydrofuran / 0.25 h / 20 °C View Scheme

1.1: sodium azide / water; acetone / 0.5 h / 20 °C / |Inert atmosphere 2.1: water; triphenylphosphine / tetrahydrofuran / 20 °C / |Inert atmosphere 3.1: tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 4.1: sodium hydroxide / ethanol / 3 h / |Inert atmosphere 4.2: |Inert atmosphere 5.1: hydrogen; bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; tris (α-naphthyl)phosphine; (3aR,8aR)-(−)-(2,2-dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine / isopropyl alcohol / 20 h / 30 °C / 18751.9 Torr / |Inert atmosphere View Scheme

sodium azide in water; acetone T=25°C; 0.166667 h;

1: 77.8 percent / dimethylformamide / 20 °C 2: hydrogen; chiral ManniPhos-based ligand / [Rh(COD)2]BF4 / CH2Cl2 / 36 h / 20 °C / 64600 Torr 3: HCl / H2O / 24 h / Heating View Scheme

Multi-step reaction with 3 steps 1: 73 percent / K2CO3 / acetone / 3 h / Heating2: 87 percent / H2O, KOH / acetone / 14 h / Ambient temperature3: 91 percent / TFAA / CH2Cl2 / 1 h / Heating